Critical Reviews in Analytical Chemistry

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Recent Advances in Fluorescent Probes for Zinc

Ions Based on Various Response Mechanisms

Jinrong Wen, Qianying Hua, Sha Ding, Aokui Sun & Yong Xia

To cite this article: Jinrong Wen, Qianying Hua, Sha Ding, Aokui Sun & Yong Xia (2023): Recent
Advances in Fluorescent Probes for Zinc Ions Based on Various Response Mechanisms, Critical
Reviews in Analytical Chemistry, DOI: 10.1080/10408347.2023.2238078

To link to this article: https://doi.org/10.1080/10408347.2023.2238078

Published online: 24 Jul 2023.

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CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY
https://doi.org/10.1080/10408347.2023.2238078

REVIEW ARTICLE

Recent Advances in Fluorescent Probes for Zinc Ions Based on Various Response
Mechanisms
Jinrong Wena, Qianying Huaa, Sha Dinga, Aokui Suna, and Yong Xiaa,b
a
School of Packaging and Materials Engineering, Hunan University of Technology, Zhuzhou, China; bCollege of Chemistry and Chemical
Engineering, Central South University, Changsha, China

ABSTRACT KEYWORDS
Zinc is a vital metal element with extensive applications in various fields such as industry, metal- Fluorescence probes;
lurgy, agriculture, food, and healthcare. For living organisms, zinc ions are indispensable, and their fluorescence mechanisms;
deficiency can lead to physiological and metabolic abnormalities that cause multiple diseases. Zinc ion detection
Hence, there is a significant need for selective recognition and effective detection of free zinc
ions. As a probe method with high sensitivity, high selectivity, real-time monitoring, safety, harm-
lessness and ease of operation, fluorescent probes have been widely used in metal ion identifica-
tion studies, and many convenient, low-cost and easy-to-operate fluorescent probes for Zn2þ
detection have been developed. This article reviews the latest research advances in fluorescent
chemosensors for Zn2þ detection from 2019 to 2023. In particular, sensors working through
photo-induced electron transfer (PET), excited state intramolecular proton transfer (ESIPT), intramo-
lecular charge transfer (ICT), fluorescence resonance energy transfer (FRET), chelation-enhanced
fluorescence (CHEF), and aggregation-induced emission (AIE) mechanisms are described. We dis-
cuss the use of various recognition mechanisms in detecting zinc ions through specific cases,
some of which have been validated through theoretical calculations.

Introduction production and transportation will be released into the

Zinc is the second most prevalent transition metal in living
organisms, following iron. It is the sole metal present in all
enzymes and has a critical role in numerous physiological
processes such as cell division, protein synthesis, DNA syn-
thesis, and the immune system. Proper regulation of free
zinc ions is crucial in maintaining homeostasis and normal
biological functioning.[1–4] However, excessive or insufficient
intake of Zn2þ can give rise to various diseases. Zinc defi-
ciency is associated with reduced immune function, stunted
growth and development, abnormal nervous system function
and development, metabolic disorders, and reproductive
abnormalities. This can lead to dental and skeletal abnor-
malities, ischemic stroke, prostate cancer, Parkinson’s dis-
ease, tuberculosis, and diabetes. Conversely, excessive levels
of zinc ions can be toxic to the body’s vital organs, includ-
ing the liver, kidneys, heart, and nervous system.[5–7] It can
also disrupt various metabolic processes, leading to abnor-
mal bone development, fat metabolism disorders, and nega-
tive impacts on the immune, reproductive and digestive
systems.[8–11] Moreover, large amounts of zinc in the envir-
onment can also cause serious pollution to the ecosystem.
Excessive discharge of zinc from daily industrial production
and agricultural activities will be carried into water and soil,
leading to water pollution and soil pollution, affecting the
health of aquatic organisms and crops. In addition, a sub-
stantial amount of zinc produced during industrial
atmosphere, polluting the air and causing harm to human
health.[12–14] Therefore, it becomes crucial to obtain a sensi-
tive and selective zinc ion detection method.
Fluorescent probes are fluorescent dyes used to detect
specific chemicals or biomolecules. They can generate a
fluorescent signal through a chemical reaction or photoexci-
tation to enable the quantitative or qualitative detection of a
target molecule.[15] A fluorescent probe usually consists of a
fluorophore, a connecting group and a recognition group.
The fluorophore is a molecule with fluorescent properties,
which can emit fluorescence signal under specific wave-
length of light excitation; the connecting group is mainly
using conjugate connection and flexible connection to con-
nect the fluorescent groups and recognition groups, gener-
ally choose short chain alkyl such as methylene; the
recognition group as the target molecule is highly specific to
the target molecule binding part. By introducing fluores-
cence probe into the sample, the recognition group com-
bines with the target molecule to activate the fluorophore,
thus generating fluorescence signal. Some fluorescent probes
also include auxiliary components, such as soluble carriers
and modified groups, which are used to improve the stabil-
ity and biocompatibility of the probe. Due to their high sen-
sitivity, excellent selectivity, fast response and simple
operation, fluorescent probes are widely used in life sciences,

CONTACT Y. Xia xiayong@hut.edu.cn School of Packaging and Materials Engineering, Hunan University of Technology, Zhuzhou 412007, China.
ß 2023 Taylor & Francis Group, LLC
2 J. WEN ET AL.
environmental testing, food safety and drug development
(Figure 1).[16–18]
To date, various fluorescent chemical sensors have been
developed for the selective detection of Zn2þ. These probes
mainly include photo-induced electron transfer (PET)[19–23],
excited state intramolecular proton transfer (ESIPT)[24–26],
intramolecular charge transfer (ICT)[27–30], fluorescence res-
onance energy transfer (FRET)[31,32], aggregation-induced
emission (AIE)[33–35] and chelation-enhanced fluorescence
(CHEF).[36–39] This review summarizes the recently reported
(2019–2023) fluorescent sensors for detecting Zn2þ and their
working methods, detailing several common recognition
mechanisms of these fluorescent sensors for the detection
of Zn2þ.
Probes based on photo-induced electron transfer
mechanism
Photo-induced electron transfer (PET) is the process by
which electrons in a molecule are transported from the
donor molecule to the acceptor molecule under photoexcita-
tion.[40] In general, when the fluorescent group is excited,
the electrons of the highest occupied molecular orbital
(HOMO) transition to the lowest unoccupied molecular
orbital (LUMO) through the radiation transition, generates
fluorescence. However, when the HOMO of the recognition
group is between the HOMO and LUMO of the fluoro-
phore, the excited electrons of the fluorophore will transfer
to the HOMO of the recognition group, so that the excited
Figure 1. Construction of fluorescent probe.
Figure 2. PET mechanism diagram.
electrons can not return to the ground state directly, result-
ing in fluorescence quenching. The fluorescence quenching
caused by this reason is called the A-PET effect. When the
LUMO of the recognition group is between the HOMO and
the LUMO of the fluorophore, it can also cause the excited
electrons to fail to return to the original HOMO, resulting
in fluorescence quenching. The fluorescence quenching
caused by this reason is called the d-PET effect. When the
identification group combines with the object to be tested,
its HOMO energy level is lower than the HOMO level of
the fluorophore, and the LUMO energy level is higher than
the LUMO level of the fluorophore, the PET effect is inhib-
ited, and the excited electrons of the fluorophore group
return directly to the ground state through the form of radi-
ation transition, thus restoring the fluorescence. Therefore,
fluorescent chemical sensors can use this PET process to
detect the object under test based on changes in fluorescence
intensity (Figure 2).[41,42]
Yan et al.[43] developed a near-infrared fluorescent probe
1, based on 2-hydrazine pyridine and dicyanisophospho-
none. Probe 1 can selectively recognize Zn2þ, but is suscep-
tible to Cd2þ interference. The fluorescence intensity of
probe 1 increased rapidly at 668 nm after the addition of
Zn2þ, with significant red fluorescence visible to the naked
eye, and reached the maximum value within 15 s, indicating
fast response speed. The detection limit was as low as
0.21 mM, reflecting high sensitivity. Mass spectrometry ana-
lysis suggested that the weak fluorescence of probe 1 is due
to the PET process from the C ¼ N part of the imide bond
to the dichyanoisoflurone group, and the isomerization of
the C ¼ N double bond. Upon adding Zn2þ, it can bind
with the N and O atoms on the probe molecule, hindering
the PET process and isomerization, thus leading to the
enhancement of emission intensity. Additionally, the probe
can be employed for the detection of Zn2þ in living cells
and drinking water (Figure 3).
Subsequently, based on probe 1, Yan and his co-
workers[44] replaced 2-hydrazine pyridine with O-phenylene-
diamine and reacted with the intermediate to synthesize a
new dicyanoisfosone-base probe 2, which can specifically

recognize Zn2þ without interference from Cd2þ. Under
365 nm UV light, the color of the solution changed from
light orange to bright red, the fluorescence intensity
increased sharply at 660 nm, and reached stable after 30 s.
Moreover, the detection limit was as low as 0.0048 mM.
Mass spectrometry analysis revealed that Zn2þ occupied the
electrons of the nitrogen atoms on the Schiff base, inhibiting
the PET from the C ¼ N double bond to the dicyanoiso-
fluoroone part, resulting in enhanced fluorescence.
Moreover, the probe displayed reliable detection perform-
ance for Zn2þ in ambient water samples and living cells
(Figure 4).
Hamzi et al.[45] designed and synthesized a phenyldihy-
drazine probe 3, with two C ¼ N-N ¼ C parts based on the
condensation reaction of phenyldihydrazine (b) with cinna-
maldehyde. The fluorescence spectra showed that probe 3
Figure 3. Sensing mechanism of probe 1 with Zn2þ and Cd2þ.[43]
Figure 4. Sensing mechanism of probe 2 with Zn2þ.[44]
Figure 5. Sensing mechanism of probe 3 with Zn2þ.[45]
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 3
had only slight fluorescence emission in dimethyl sulfoxide
(DMSO) solution. However, upon the addition of Zn2þ,
probe 3 exhibited a fluorescence emission peak at a wave-
length of 451 nm, and the fluorescence intensity increased
152 times with increased Zn2þ concentration; the detection
limit was about 250 mM. Due to the presence of two C ¼ N-
N ¼ C parts, a bunch of solitary pair electrons on the N
atom were transferred, and the PET process occurred. When
probe 3 was complexed with Zn2þ, the resulting complex
C ¼ N was enhanced in isomerization, and the molecular
structure was enhanced in rigidity, which resulted in a larger
chelation-enhanced fluorescence effect. At this time, the
PET process was inhibited, resulting in a significant increase
in fluorescence (Figure 5).
Enbanathan et al.[46] reported that their fluorescent probe
4, developed using benzothiazole and imidazopyridine
4 J. WEN ET AL.
derivatives, exhibits weak fluorescence at 489 nm in ACN:
H2O (8:2, v/v) solution. However, upon addition of Zn2þ,
the probe showed strong “ON” fluorescence enhancement at
473 nm, and the fluorescent band at 489 nm increased with
increased Zn2þ concentration, with a fluorescence color shift
from blue to bright green. The response time was as low as
10 s and the detection limit was 0.0236 mM. Through both
experimental tests and density functional theory (DFT) cal-
culations, they proposed a PET fluorescence enhancement
mechanism. As the imidazole pyridine unit is rich in elec-
trons, it acts as an electron donor, and through the PET
process, the fluorescence of the benzothiazole unit is
quenched. However, upon addition of Zn2þ to form a com-
plex, the PET process is inhibited, leading to fluorescence
recovery. Notably, probe 4 can also be utilized to detect the
concentration of Zn2þ in real water samples and living cells
(Figure 6).
Ahmad et al.[47] designed and synthesized two fluorescent
probes 5 and 6 containing 2,4-dinitrobenzene and 1,8-naph-
thalimide, respectively, using 2,2-dimer amine (DPA) as the
receptor unit. In aqueous solution, when excited at 350 nm,
probe 5 and probe 6 exhibited fluorescence enhancement at
438 nm and 428 nm, respectively, with 4.7-fold and 6-fold
enhancement and a limit of detection (LOD) of 0.0656 mM
and 0.107 mM. In the absence of Zn2þ, the PET process
quenches the fluorescence by transferring electrons from the
electron donor to the excited fluorophore. However, as the
concentration of Zn2þ gradually increases, the zinc complex
was produced, which prevented the PET process from
occurring. By DFT calculations, it was determined that the
fluorescence enhancement of the sensor was attributed to
binding with Zn2þ. The strong binding of Zn2þ enhanced
the electronic coupling between the HOMOs and the
LUMOs to form highly excited states with higher probabil-
ities of electron transition. This was found to be the reason
for the observed fluorescence enhancement rather than a
conformational change in the molecules (Figure 7).
Panchenko et al.[48] reported a Schiff base probe 7
derived from 4-methoxy-n-amino-1, 8-naphthalimide and
salicylaldehyde as a fluorescent probe for Zn2þ. The fluores-
cence of probe 7 in acetonitrile solution was initially weak
Figure 6. Sensing mechanism of probe 4 with Zn2þ.[46]
at 437 nm. However, the addition of Zn2þ significantly
enhanced the fluorescence intensity at 455 nm. The frontier
molecular orbital of probe 7 was then calculated using the
PM6 method. The fluorescence enhancement was attributed
to a PET process that occurs in the excited state, which
quenched the fluorescence of probe 7. Upon binding with
Zn2þ, the power supply of the salicylate receptor group
decreased, resulting in enhanced fluorescence (Figure 8).
It was found that methylene bonds in zinc chemosensors
play a very important role in controlling fluorescence sens-
ing properties. Based on this, Maity et al.[49] synthesized two
Schiff base compounds, probe 8 and probe 9, by condensing
2-hydroxybenzaldehyde and 2-hydroxy-5-methylbenzalde-
hyde with 2-hydrazinoquinoline, respectively. Probe 8 exhib-
ited a moderately intense emission peak at 490 nm, and its
fluorescence intensity increased by approximately 4.5-fold
upon the addition of Zn2þ. In comparison, probe 9 dis-
played weak fluorescence at 502 nm, which was red-shifted
to 515 nm after the introduction of Zn2þ. As a result, the
fluorescence intensity increased by nearly 30-fold, leading to
a distinguishable green fluorescence when irradiated by UV
light. Probe 9 also exhibited a detection limit of 0.2206 mM
for Zn2þ. The introduction of the electron-donating group
methyl greatly improves the sensing efficiency of the probe.
Theoretical calculations using DFT method revealed that the
fluorescence enhancement is caused by the inhibition of
PET and C ¼ N isomerization from the complexation of
probe 9 with Zn2þ. Additionally, probe 9 has been imple-
mented in live cell imaging studies (Figure 9).
Kirthika et al.[50] synthesized a fluorescence sensor probe
10 based on pyrene and malonyl hydrazine groups that can
selectively detect Zn2þ in the presence of Cd2þ. A weak
fluorescence emission of probe 10 at 450 nm was observed
in the buffer solution of CH3CN:H2O (1:1, v/v). When Zn2þ
was added into the solution, the fluorescence was enhanced
nearly 9 times, and the dark blue fluorescence was visible in
the solution. The detection limit was 0.0051 mM, indicating
that probe 10 had high selectivity and sensing efficiency for
Zn2þ. By theoretical calculation using DFT method, it is
proved that the weak fluorescence of probe 10 is due to the
transfer of lone pair electrons on imine nitrogen to pyrene

Figure 7. Sensing mechanism of probe 5 and probe 6 with Zn2þ.[47]
Figure 8. Sensing mechanism of probe 7 with Zn2þ.[48]
fluorophore, and in the presence of Zn2þ, the probe is com-
plexed with Zn2þ, which prevents the PET effect and thus
enhances the fluorescence. In addition, the low toxicity of
the probe allows it to be used to detect Zn2þ concentrations
in living cells (Figure 10).
Compared to small molecule fluorescent probes, peptide-
as-receptor fluorescent probes have good water solubility,
biocompatibility, high chemical stability and low toxicity,
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 5
and with a simple solid-phase synthesis method for peptides,
peptide fluorescent chemosensors can bind strongly to metal
ions to produce a rapid fluorescence response. Based on
this, Wang et al.[51] designed and synthesized a peptide-
based fluorescent sensor, probe 11, with a dansyl group as
the fluorophore coupled to a histidine and an imidazole
group as the recognition moiety. The fluorescence of this
probe was initially very weak, only after the addition of
6 J. WEN ET AL.
Figure 9. Sensing mechanism of probe 8 and probe 9 with Zn2þ.[49]
Figure 10. Sensing mechanism of probe 10 with Zn2þ.[50]
Zn2þ, a 5-fold enhancement of the fluorescence was
observed, with bright green fluorescence in solution and a
detection limit of 0.01925 mM. The imidazole moiety has
donor capacity during the PET quenching of the dansyl
emitter. Through titration experiments and mass spectrom-
etry, it was revealed that the probe fluorescence quenching
was a result of the transfer of electrons from the imidazole
moiety and histidine as donors to the dansyl moiety under
photoexcitation, resulting in the fluorescence quenching of
the dansyl moiety. With the addition of Zn2þ, the imidazole
moiety ligated with the metal ion, inhibiting the PET pro-
cess, and subsequently restoring the fluorescence of the dan-
syl moiety. In addition, probe 11 can be used for Zn2þ
tracking under live cell imaging (Figure 11).
Subsequently, the team of Wang[52] designed another
peptide chemosensor probe 12 with dansyl as the electron
acceptor and histidine as the electron donor. Probe 12
showed no significant fluorescence response to other metal
ions in aqueous solution, while a significant fluorescence
enhancement was observed upon the addition of Zn2þ, and
the detection limit for Zn2þ was 0.0368 mM with high sensi-
tivity. According to theoretical calculation, the fluorescence
quenching of probe 12 was due to the electron transfer from
histidine to dansyl group in the excited state. After binding
with Zn2þ, PET was inhibited, and fluorescence was
recovered later. Due to its low toxicity and good biocom-
patibility, Probe 12 can be successfully used to monitor
Zn2þ in living cells (Figure 12).
Liu et al.[53] designed a novel fluorescent sensor called
Probe 13, with iminoethoxyacetic acid as the acceptor and
4-amino-1,8-naphthalimide as the fluorophore. The probe
emitted faint green fluorescence at 550 nm under excitation
at 470 nm, which was enhanced 5-fold by the addition of
Zn2þ, with a detection limit of 0.772 mM. Mass spectromet-
ric analysis and theoretical calculations revealed that the
probe underwent an electron transfer from the acceptor imi-
noethoxyacetic acid to the fluorophore 4-amino-1,8-naph-
thalimide upon photoexcitation, resulting in a fluorescence
quenching. The addition of Zn2þ restored fluorescence by
coordinating with the probe acceptor, inhibiting the PET
process. In addition, the probe can be successfully used for
live cell imaging (Figure 13).
Following their previous work, the group of Liu[54] syn-
thesized a new 4-amino-1,8-naphthalimide fluorescent che-
mosensor probe 14 by introducing both iminoacetic acid
and iminoethoxyacetic acid as receptors on the basis of the
probe. Similar to the prior probe, Probe 14 emits faint green
fluorescence at 550 nm upon excitation at 470 nm. However,
the addition of Zn2þ boosts the fluorescence by approxi-
mately 20 times, resulting in remarkable sensing

Figure 11. Sensing mechanism of probe 11 with Zn2þ.[51]
Figure 12. Sensing mechanism of probe 12 with Zn2þ.[52]
performance with a detection limit of 4.25 mM. Mass spec-
trometric analysis and theoretical calculations revealed that
under photoexcitation of the probe, the acceptor iminoacetic
acid and iminoethoxyacetic acid fractions rapidly transfer
electrons to the fluorophore 4-amino-1,8-naphthalimide,
leading to a fluorescence quenching. When Zn2þ is present,
it coordinates with the probe acceptor, thereby inhibiting
the PET process and restoring fluorescence. In addition, the
probe can be applied to detect Zn2þ concentrations in aque-
ous solutions and in living cells (Figure 14).
The PET mechanism is commonly utilized in fluorescent
probes that contain recognition groups with lone pair of
electrons, especially N and S, to enable flexible connection
with the fluorescent groups. Upon photoexcitation, the lone
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 7
pair of electrons from the recognition group is transferred
to the fluorescent group, leading to fluorescence quenching.
However, interaction of the probe molecule with metal ions
weakens the PET effect and restores fluorescence. The PET
mechanism finds application in designing OFF-ON type
fluorescent chemical sensors.[55]
Probes based on excited state intramolecular
proton transfer mechanism
Excited state intramolecular proton transfer (ESIPT) refers
to the phenomenon that the electron transition from the
ground state to the excited state occurs when the molecule
8 J. WEN ET AL.

Figure 13. Sensing mechanism of probe 13 with Zn2þ.[53]

Figure 14. Sensing mechanism of probe 14 with Zn2þ.[54]

is photoexcited, in which proton transfer occurs between the

proton-donating group and the proton-accepting group in
the excited state, resulting in the formation of the tauto-
mer.[56] The common tautomerism is mainly enol and keto
tautomerism. The equilibrium tends to be keto structure
when the aromatic ring has electron-absorbing substituents
and enol structure when the aromatic ring has electron-
donating substituents. Studies have shown that the molecule
prefers to adopt the keto form in polar solvents, while the
enol form is more stable in non-polar solvents. In ethanol
or acidic solvents, Schiff base molecules can form intermo-
lecular hydrogen bonds with solvent molecules, which pro-
vides the basis for the intramolecular proton transfer of
Schiff base, and also improves the stability of ketone struc- Figure 15. ESIPT mechanism diagram.
ture in polar solvents to a certain extent.[57,58] When the
excited state tautomer returns to the ground state, the mol-
ecule undergoes a ground state intramolecular proton trans- Singh et al.[62] developed the first two silicon methane-
fer (GSIPT) reaction via a low-energy barrier process, linked Schiff base fluorescent probes, probe 15 and probe
leading to its conversion into a normal form.[59] While 16, as well as hybrid silica nanoparticles probe 17 of probe
ESIPT is typically associated with isomerization of photoex- 15, utilizing the ESIPT method. Upon UV excitation at
cited states, the GSIPT reaction no longer requires the 350 nm, probe 15, probe 16 and probe 17 showed fluores-
involvement of photoexcitation but instead involves charge cence at 423 nm, 406 nm, and 408 nm, respectively, which
redistribution and the formation of new chemical bonds significantly increased upon the addition of Zn2þ, with
through intramolecular proton transfer in the ground state detection limits of 0.1255 mM, 0.623 mM, and 0.0243 mM,
(Figure 15).[60,61] respectively. The mass spectrometry analysis demonstrated

that the weak fluorescence of probe 15 and probe 16 was
due to the rapid C ¼ N isomerization and ESIPT process.
However, when the molecule was coordinated with Zn2þ
and imine nitrogen and phenolic hydroxyl group, it was
restricted, preventing the C ¼ N bond isomerization and
ESIPT process. In addition, probe 17 exhibited high binding
strength to Zn2þ, low detection limit, low cytotoxicity, and
excellent antioxidant activity (Figure 16).
A fluorescence chemical sensor probe 18 synthesized by
linking diaromatic ethylene compounds with coumarin fluo-
rophore via a condensation reaction was reported by Mei
et al.[63] Probe 18 exhibited very weak green fluorescence at
360 nm excitation in acetonitrile solution. However, upon
addition of Zn2þ, the fluorescence emission peak shifted
from 539 nm to 518 nm, and the emission intensity
increased by 18 times, resulting in a change in solution color
from light green to bright cyan, with a LOD of 0.014 mM for
Zn2þ detection. The weak fluorescence of the probe was due
to the ESIPT process of the Schiff base molecular hydroxyl
group adjacent to the C ¼ N nitrogen atom. Binding of
Zn2þ to the probe inhibited the ESIPT process, leading to
enhanced fluorescence. In addition, the probe can also be
employed for the detection of Mg2þ and has been success-
fully applied to the detection of test strips and live cell imag-
ing (Figure 17).
Figure 16. Sensing mechanism of probe 15–17 with Zn2þ.[62]
Figure 17. Sensing mechanism of probe 18 with Zn2þ.[63]
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 9
Behura et al.[64] synthesized a Schiff base molecular probe
19 using the reaction of 2-hydroxybenzaldehyde and 2,4-
dinitrophenylhydrazine. When excited at 340 nm, the probe
emitted weak fluorescence at approximately 530 nm in a
H2O/DMSO (90:10, v/v) solution. Upon addition of Zn2þ,
the fluorescence significantly increased and changed from
red to yellow, with a detection limit of 0.011 mM. Mass spec-
trometry analysis and theoretical calculations revealed that
the weak fluorescence of probe 19 was due to the ESIPT
process of the probe’s imine group N atoms and phenolic
hydroxyl H atoms in the polar solvent DMSO, along with
competition between solution and intermolecular hydrogen
bonds which inhibited ESIPT. However, upon addition of
Zn2þ, Zn2þ and the probe obstructed the ESIPT process,
leading to fluorescence recovery. Additionally, the prob was
highly selective for Zn2þ in the solid phase and was useful
for live-cell imaging and solid-state Zn2þ detection
(Figure 18).
A water-soluble Schiff base chemosensor probe 20 was
designed by Theetharappan et al.[65] The probe itself exhib-
ited two very low-intensity emission peaks at 491 nm and
534 nm. The addition of Zn2þ significantly enhanced the
peaks at 491 nm and 534 nm, with a detection limit of
0.00706 mM. Theoretical calculations indicated that under
light excitation, an intramolecular hydrogen bond was
10 J. WEN ET AL.
Figure 18. Sensing mechanism of probe 19 with Zn2þ.[64]
Figure 19. Sensing mechanism of probe 20 with Zn2þ.[65]
formed between the phenol hydroxyl group and imine N,
and the ESIPT process occurred, generating ketone isomers.
After the addition of Zn2þ, complexation with the probe
increased the molecular rigidity and inhibited the isomeriza-
tion of ESIPT and C ¼ N, resulting in enhanced fluores-
cence. This probe also showed high recognition for Al3þ,
and it could be used in an aqueous medium for the neutral-
ization of human glioblastoma U87, as well as for Al3þ and
Zn2þ detection in hepatocellular carcinoma C3A cells
(Figure 19).
Fan et al.[66] synthesized a quinoline-derived Schiff base
fluorescence probe 21, which exhibited negligible fluores-
cence upon excitation at 375 nm. When Zn2þ was added,
the fluorescence emission of probe 21 in the ethanol solu-
tion significantly increased at 450 nm, and the solution
changed from colorless to blue. The team of Fan hypothe-
sized that the fluorescence enhancement was due to the
inhibition of the PET process by the complexation of the
metal and the probe. Later, through theoretical calculations,
we[67] demonstrated that under the photoexcitation, probe
21 molecules underwent ESIPT instead of the PET process,
and upon complexation of Zn2þ with the probe, the rigidity
and planarity of the complex increased, inhibiting the ESIPT
process, as well as C ¼ N isomerization, ultimately leading to
fluorescence enhancement (Figure 20).
A Schiff base fluorescent probe 22 based on benzothia-
zole was presented by Wu et al.[68] Probe 22 displayed
strong emission at 570 nm when excited at 362 nm in a
H2O/MeOH (2:3, v/v) mixture. However, the addition of
Zn2þ led to a blue shift in the emission peak to 480 nm, and
the solution underwent a color change from orange to green
with a detection limit of 0.377 mM. The observed double
fluorescence phenomenon was attributed to the ESIPT pro-
cess, causing isomerization between the enol and keto forms.
Upon Zn2þ addition, the ESIPT process was inhibited, and
molecule rigidity increased, leading to enhanced chelate
fluorescence. Subsequently, Zhuang et al.[69] performed
detailed theoretical calculations using the DFT method and
obtained spectroscopic data in good agreement with the
experiments. Additionally, they explained the photochemical
behavior of the ESIPT process and specific photophysical
changes upon Zn2þ ion detection by the probe at a molecu-
lar level, using structural optimization, IRI analysis, FMOs
analysis, and potential energy curve scanning (Figure 21).
Fluorescent probes with ESIPT properties are mostly
found in Schiff base molecules, owing to the strong binding
between the imine C ¼ N bond and transition metals due to
the presence of heteroatoms such as N atoms. Moreover, the
ease of synthesis of Schiff base molecules makes them widely
popular in this application. As such, Schiff base molecules
serve as excellent ligands for forming stable complexes with
metal ions through metal ion coordination.[70,71]
Probes based on intramolecular charge transfer
mechanism
Intramolecular charge transfer (ICT) refers to the process in
which electrons inside a molecule are transferred from one
atom or functional group to another, thereby changing the
charge distribution of the molecule.[72] The recognition
group of this kind of probe has the ability to either push or
pull electrons and is conjugated to the fluorophore. Upon
interaction with the object to be tested, the recognition
group’s electron mobility changes, leading to a change in the
molecular dipole distance, and subsequently causing a shift
in the fluorescence spectrum. In general, if the cation is
coordinated with the acceptor group, its electron-absorbing
ability would enhance, which increases the intramolecular

Figure 20. Sensing mechanism of probe 21 with Zn2þ.[66]
Figure 21. Sensing mechanism of probe 22 with Zn2þ.[68]
dipole distance and makes the fluorescence spectrum red-
shift (Figure 22).[73,74]
Shirbhate et al.[75] developed and synthesized a fluores-
cent sensor probe 23, and its enantiomer probe 24. Upon
addition of Zn2þ to the DMSO:H2O (4:1, v/v) solution, the
fluorescence of the two probes significantly increased at
550 nm, and the circular dichroism (CD) spectrum were
completely opposite. These changes in the fluorescence and
CD spectra stemmed from the ICT process, where the com-
bination of Zn2þ and the probe altered the dihedral angle
between the bisnaphthol groups. Additionally, Probe 23
exhibited potential for Zn2þ imaging within cells
(Figure 23).
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 11
Based on the 8-hydroxyquinoline and 7- (diethylamine)
coumarin unit, a fluorescent probe 25 was synthesized by
Kang et al.[76] The coumarin unit acted as an electron donor
and the quinoline part as an electron acceptor, forming a typ-
ical “push-pull” structure. In acetonitrile solution, the probe
emitted at 469 nm. Upon addition of Zn2þ, the fluorescence
wavelength of the probe gradually redshifted to 489 nm, and
the fluorescence color changed from blue to bright green.
The detection limit of the probe for Zn2þ was 0.6 mM, indi-
cating high sensitivity. Theoretical calculations using the DFT
method revealed that the fluorescence wavelength and color
changes of the probe were attributed to the ICT process from
the coumarin unit to the quinoline unit during interaction
12 J. WEN ET AL.

Figure 22. ICT mechanism diagram.

Figure 23. Structure of probe 23 and probe 24.[75]

Figure 24. Sensing mechanism of probe 25 with Zn2þ.[76]

with Zn2þ under photoexcitation, which led to the recombin- and detect, and its significant color change upon reaction
ation of the molecular electronic structure and resulting fluor- with Zn2þ suggests that it can be utilized to create test paper
escence wavelength redshift. The probe is simple to prepare for rapid detection of zinc ions (Figure 24).

According to the recommendations of the World Health
Organization, the amount of zinc in drinking water should
not exceed 5 mg/L (ppm) or 76 nM. However, it has been a
challenge to develop effective methods for detecting micro
or ultra-trace amounts of zinc. In light of this, Patawanich
et al.[77] synthesized a helicene-derived fluorescent probe 26.
At 373 nm excitation, maximum fluorescence intensity of
the probe was observed at 531 nm in HEPES buffer: MeOH
(3:2, v/v) solution. After the addition of Zn2þ, the probe’s
emission spectrum shifted from 531 nm to 456 nm, resulting
in a 4-fold increase in fluorescence, and a color change from
orange to blue. The detection limit of the probe was found
to be as low as 0.029 mM, which is substantially below the
WHO recommended limit for the amount of Zn2þ in drink-
ing water. Theoretical calculations using the DFT method
revealed that the fluorescence enhancement and wavelength
shift of the probe were due to the promotion of the ICT
process after complexing with Zn2þ. This caused corre-
sponding shifts in fluorescence wavelength and intensity.
Moreover, the sensor is not only useful for detecting trace
amounts of zinc in drinking water but also has practical
applications in biological imaging of living cells such as liver
and brain cells using fluorescence (Figure 25).
Zhang et al.[78] successfully synthesized two highly select-
ive fluorescent probes for Zn2þ detection, probe 27 and
probe 28, by combining syringaldehyde with rhodamine B
and rhodamine 6G hydrazide, respectively. The rhodamine
dye serves as the fluorophore, while syringaldehyde func-
tions as the recognition group. In HEPES buffer, neither
UV-Visible nor fluorescence emission spectra showed any
visible peaks for probe 27 and 28. However, when Zn2þ was
Figure 25. Sensing mechanism of probe 26 with Zn2þ.[77]
Figure 26. Structure of probe 27 and probe 28.[78]
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 13
added, the solution color changed from colorless to purple,
and the UV-Visible absorption band was observed at
527 nm and 558 nm, respectively. Additionally, the two
probes showed 10-fold fluorescence enhancement at 585 nm
and 557 nm, with the detection limit of probe 27 and probe
28 toward Zn2þ was 0.00018 mM and 0.00019 mM, respect-
ively. Theoretical calculations using the DFT method
revealed that the ICT process occurs in the molecular orbit
of Zn2þ and the probe, indicating that the binding of the
probe to Zn2þ causes a charge transfer process in the rhoda-
mine fluorophore. Moreover, both probes are suitable for
tracking the concentrations in live Hela and MCF-7 cells
using fluorescence imaging (Figure 26).
Aziz et al.[79] synthesized a novel Schiff base fluorescence
sensor, probe 29, based on 2-Hydroxy-1-naphthaldehyde
and 2-aminothiazole. The probe exhibited weak fluorescence
emission at 586 nm. Upon addition of Zn2þ, fluorescence
was enhanced by approximately 5-fold, and the detection
limit was 0.0311 mM. The theoretical calculations by DFT
method supports that probe 29 can be used as a bidentate
ligand to coordinate the metal, with the probe’s fluorophore
undergoing the charge transfer from the donor to the
acceptor under photoexcitation, resulting in an ICT process.
In the presence of Zn2þ, the hydroxyl O atom and azome-
thine N atom formed a conjugate leakage, which restricted
the ICT process. Furthermore, the probe had excellent cell
membrane permeability and was capable of detecting Zn2þ
concentrations in living cells (Figure 27).
Li et al.[80] designed a highly water-soluble fluorescent
probe 30, based on the quinoline group. The probe exhib-
ited a weak emission peak at 455 nm under two-photon
14 J. WEN ET AL.
Figure 27. Sensing mechanism of probe 29 with Zn2þ.[79]
Figure 28. Sensing mechanism of probe 30 with Zn2þ.[80]
excitation at 750 nm, and upon addition of Zn2þ, the emis-
sion was red-shifted to 515 nm. The probe had a detection
limit of 0.02–0.03 mM for Zn2þ, with a response time of less
than 2 s and high sensitivity. The change in the fluorescence
spectrum was mainly attributed to the ICT process that
occurred after the probe was coordinated with Zn2þ. This
process increased the intramolecular dipole moment and
resulted in a red shift of 60 nm in the fluorescence spectrum.
Moreover, the probe could be used for rapid detection of
Zn2þ in both living cells and zebrafish larvae (Figure 28).
Jiang et al.[81] used 2,6-bisbenzimidazolylpyridine (BBP)
as the skeleton of the fluorescence sensor, and introduced
two hydrophilic alkyl hydroxyl groups to obtain a highly
water-soluble fluorescence probe 31. The probe exhibited
weak fluorescence with an emission peak at 383 nm. Upon
addition of Zn2þ, the solution changed from colorless to
blue and the emission peak was red-shifted to 415 nm. The
probe had a detection limit of 0.183 mM toward Zn2þ, with
a response time of about 4 minutes. According to the theor-
etical calculations by DFT method, the benzimidazole group
rotation was inhibited after the complexation of the probe
with Zn2þ, and the molecular planarity was greatly
improved. In addition, the charge of the probe was trans-
ferred from the benzimidazole portion to the pyridine ring
on a large scale, and the HOMO-LUMO gap of the zinc
complex was smaller than that of the probe, indicating that
the red shift was due to the ICT process. Moreover, the
probe is widely used in the detection of Zn2þ in real water
samples and multifunctional test paper (Figure 29).
In recent years, although fluorescence imaging, or optical
imaging, has made progress in imaging depth of tissues,
challenges of tissue scattering and autofluorescence hinder
the achievement of optimal deep tissue imaging. However,
the latest study of photoacoustic imaging (PA) has improved
this issue. Based on this, Fang et al.[82] designed a HD dye-
based near-infrared PA sensor, probe 32. Probe 32 is a mol-
ecule with a noticeable intramolecular charge transfer (ICT)
property, witn an indolinium Nþ acting as the electron-
withdrawing group and hydroxyl group as the electron-
donating group. In HEPES buffer, the probe had an intense
emission peak at 703 nm, which was blue-shifted to 697 nm
upon addition of Zn2þ. The 1H NMR spectra of Zn2þ titra-
tion and theoretical calculations found that the fluorescence
enhancement was due to the binding of Zn2þ to the probe
coordinates the oxygen atoms of the phenolic hydroxyl
group with Zn2þ, reducing the ICT effect from the phenolic
hydroxyl group to indium. Furthermore, this probe exhib-
ited great potential in both live cells and in vivo PA Zn2þ
imaging and Zn2þ monitoring in mitochondria (Figure 30).
The ICT mechanism is commonly utilized for structures
that have electron-donating and electron-accepting groups
conjugated together. The recognition group is usually a part

Figure 29. Sensing mechanism of probe 31 with Zn2þ.[81]
Figure 30. Sensing mechanism of probe 32 with Zn2þ.[82]
of the electron-donating or electron-accepting group, so that
upon detection of the target substance, the push-pull elec-
tron capacity of the entire system changes, leading to charge
redistribution and a change in the absorption spectrum.
This results in red-shifted fluorescence emission, facilitating
detection.[83]
Probes based on chelation-enhanced fluorescence
mechanism
Chelation-enhanced fluorescence (CHEF) is based on the
principle of modifying the structure and charge distribution
of ligand molecules through chemical binding with specific
metal ions, leading to changes in the intensity and nature of
the fluorescence signal.[84] In general, ligands in fluorescent
probes can select molecules with high selectivity and affinity
to form complexes with target metal ions, thus enabling
selective recognition and detection of metal ions. In the
coordination between the chelating ligand and metal ion,
some electrons transfer from the ligand to the metal ion,
forming a more stable structure that alters the photophysical
properties of the fluorescent probe.[39,85]
Moradi et al.[86] synthesized a fluorescent probe 33 based
on 2-aminobenzothiazole and 2-bromoacetophenone. In the
DMSO/H2O (95:5, v/v) solution, the probe emitted weak
fluorescence at 404 nm. However, the fluorescence was
enhanced more than 12-fold by the addition of Zn2þ, with a
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 15
detection limit of 0.03 mM and high sensitivity. The intro-
duction of electron-donating groups such as methoxy on the
phenyl group of the probe enhanced its coordination with
the Zn2þ. When Zn2þ is coordinated to the nitrogen and
oxygen atoms of the probe, the flatness and rigidity of the
molecules are increased, and the free rotation is restricted,
and eventually, p-coupling between them is increased. This
phenomenon, known as CHEF, leads to enhanced fluores-
cence. Finally, this probe can be used for the real-time
detection of Zn2þ in aqueous environments (Figure 31).
Probes with narrow Stoke shifts that exhibit short-wave
emission are susceptible to self-absorption and spontaneous
fluorescence interference. These qualities are unfavorable for
biological imaging and can negatively impact the sensitivity
of probes. To overcome these limitations, Zhang et al.[87]
synthesized a novel near-infrared fluorescent probe 34,
based on dicyanisophosphorone and dimeric amine, in
which dicyanisophosphorone serves as the recognition group
and DPA is a Zn2þ chelating ligand commonly used in this
context. In the HEPES buffer, the probe emitted an
extremely weak fluorescence. However, upon the addition of
Zn2þ, the fluorescence at 660 nm was enhanced as the solu-
tion color changed from colorless to light red, and the
response time was within 20 s. The chelation of Zn2þ with
the ligand released the hydroxyl group as a strong electron
donor, and the CHEF effect initiated the ICT process, which
extended the conjugation of the whole molecule, resulting in
fluorescence enhancement. In addition, the probe can detect
16 J. WEN ET AL.
Figure 31. Sensing mechanism of probe 33 with Zn2þ.[86]
Figure 32. Sensing mechanism of probe 34 with Zn2þ.[87]
Figure 33. Sensing mechanism of probe 35 with Zn2þ.[88]
the change in concentration of Zn2þ in living cells
(Figure 32).
A benzimidazole Schiff base chemosensor probe 35 was
synthesized by Orhan et al.[88] After the addition of Zn2þ,
the fluorescence emission of the probe at 457 nm was
enhanced about 100-fold, and the solution became daz-
zlingly white under UV light. The detection limit of probe
35 toward Zn2þ was 0.148 mM. The significant fluorescence
enhancement is due to the enhanced rigidity and planarity
of the zinc complex, limiting the intramolecular rotation
and inhibiting the C ¼ N isomerization process, producing a
strong CHEF effect. Moreover, the probe can be very easily
to directly measure Zn2þ concentration in tap water
(Figure 33).
Another benzimidazolyl Schiff base fluorescent probe 36
was designed and synthesized by Kim et al.[89] Under UV
excitation at 375 nm, the probe had negligible fluorescence
emission, but upon addition of Zn2þ to the solution, signifi-
cant blue fluorescence was emitted at 447 nm. The detection
limit was 2.26 lM, which is much lower than the WHO
standard. Theoretical calculations using the DFT method
confirmed that the enhanced fluorescence was due to the
CHEF effect resulting from the coordination of the probe
with Zn2þ. This process inhibited the isomerization and
intramolecular rotation of the C ¼ N structure, reducing
energy dissipation through non-radiative processes.
Additionally, the probe is effective in determining the con-
centration of Zn2þ in water samples and live zebrafish
(Figure 34).
Kim and his team[90] then designed another benzyl fluor-
escent chemosensor, probe 37, resulting from the condensa-
tion of benzyl carbamate and salicylaldehyde, for the
detection of Zn2þ in water samples and zebrafish. Initially,
the probe exhibited weak fluorescence at 452 nm, but upon

Figure 34. Sensing mechanism of probe 36 with Zn2þ.[89]
Figure 35. Sensing mechanism of probe 37 with Zn2þ.[90]
the addition of Zn2þ, the fluorescence was significantly
enhanced, resulting in a noticeable blue color of the solution
and achieving a detection limit of 1.12 lM. The structures of
the probe and the zinc complex were optimized by the
method of DFT. It was shown that the fluorescence enhance-
ment was due to the CHEF effect generated by the coordin-
ation of Zn2þ with the N and two O atoms of the probe
imine group, which inhibited the isomerization of C ¼ N and
other non-radiative pathways. In addition, the probe can be
used to image Zn2þ in zebrafish and test strips (Figure 35).
Zhang et al.[91] designed a fluorescent probe having two
Schiff base moieties, probe 38, by condensing two aldehyde
precursor compounds 2. Initially, the probe had minimal
fluorescence emission in the solution. However, after adding
Zn2þ, the fluorescence intensity increased significantly by 15
times at 490 nm, and the solution changed from yellow to
yellowish green, with a detection limit of 0.42 mM. The
fluorescence enhancement mechanism was analyzed through
mass spectrometry and theoretical calculations. It was dis-
covered that the chelation of the probe with Zn2þ caused its
hydrolysis into two molecular compounds 2 of its precursor,
followed by coordination with Zn2þ to form a more stable
heterodimetallic complex, leading to the opening of the
fluorescence response. Moreover, the probe can rapidly
detect Zn2þ both in vitro and in live cells (Figure 36).
Chae et al.[92] designed a fluorescent probe 39 consisting
of 2,20 -(ethylenedioxy)bis(ethylamine) linked to two quin-
oline groups. The fluorescence of the probe was very weak
initially. After the addition of Zn2þ, the fluorescence was
significantly enhanced at 493 nm, and the solution changed
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 17
from colorless to bright blue-green, achieving a detection
limit of 0.27 lM. Theoretical calculations using the DFT
method revealed that Zn2þ was solely ligated with one quin-
oline group of the probe, and the weak fluorescence was
attributed to its flexible structure leading to the dissipation
of excitation energy in non-radiative transitions such as
vibration and rotation. The CHEF effect produced by Zn2þ
and the probe increased the molecular rigidity, leading to
enhanced fluorescence. Furthermore, experiments with HeLa
cells and zebrafish indicate that probe 39 can also be used
to monitor Zn2þ in organisms (Figure 37).
Subsequently, Chae and his team[93] synthesized another
quinoline-based fluorescent probe 40. As the concentration
of Zn2þ increased, the fluorescence of the probe continu-
ously enhanced at 495 nm, and the solution changed from
colorless to light green, achieving a detection limit of
0.53 lM. Mass spectrometry analysis and theoretical calcula-
tions revealed that, similar to the previous probe, Zn2þ com-
bined with one side of the quinoline part, producing the
CHEF effect, which greatly enhanced the molecular flatness
and rigidity of the complex, suppressed the non-radiative
energy dissipation pathway, and improved fluorescence.
Moreover, the probes could be utilized for detecting Zn2þ in
both test kits and real samples (Figure 38).
Chemical sensors utilizing the CHEF mechanism typically
incorporate conjugated units into their semi-rigid structure
and integrate them into rigid, coplanar conjugated systems
by metal coordination. As a result, the CHEF mechanism is
extensively utilized for fluorescence detection and quantita-
tive analysis of metal ions.[94]
18 J. WEN ET AL.

Figure 36. Sensing mechanism of probe 38 with Zn2þ.[91]

Figure 37. Sensing mechanism of probe 39 with Zn2þ.[92]

Figure 38. Sensing mechanism of probe 40 with Zn2þ.[93]

Probes based on fluorescence resonance energy
transfer mechanism
Fluorescence resonance energy transfer (FRET) occurs in
molecules that contain two fluorescent groups, where the
absorption peak of one fluorescent group overlaps with the
emission peak of another fluorescent group, and the distance
between them is no more than 10 nm. Upon photoexcita-
tion, the donor-acceptor fluorophore interactions enable the
transfer of energy from the donor to the acceptor in a non-
radiative form (Figure 39).[95]

Yu et al.[96] reported a peptide-based fluorescence sensor
probe 41 containing six amino acids, with the dansyl group
as the fluorophore acceptor and the tryptophan residue as
the donor. In the HEPES buffer solution, when the excitation
wavelength was set to 295 nm, two fluorescence peaks
appeared at 519 nm and 362 nm. After the addtion of Zn2þ,
the fluorescence emission intensity of the probe at 519 nm
gradually increased, and the fluorescence lifetime of the
probe increased by 3 times compared with that before adding
Zn2þ. On the contrary, the fluorescence emission intensity
and fluorescence lifetime at 362 nm decreased gradually as
the concentration of Zn2þ increased. When excited at
330 nm, the emission peak only appeared at 519 nm, and the
fluorescence was enhanced with increasing Zn2þ concentra-
tion. The probe displayed a response time to Zn2þ of
1 minute, with a detection limit of 0.033 lM. The solution
transitioned from colorless to light green, showcasing excel-
lent response speed and sensitivity. Furthermore, the probe
was suitable for detecting Zn2þ in HeLa cells. The alterations
in fluorescence spectra and fluorescence lifetime decay were
observed before and after the probe’s binding to Zn2þ under
295 nm excitation. These changes provided evidence of the
energy transfer process between the tryptophan residue and
Figure 39. FRET mechanism diagram.
Figure 40. Structure of probe 41.[96]
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 19
the dansyl group of the probe and Zn2þ. This finding was
also verified by different approaches such as mass spectrom-
etry analysis and molecular modeling (Figure 40).
A fluorescent sensor probe 42 was synthesized using
phenothiazine as the donor linked to the acceptor rhoda-
mine by Karmegam et al.[97] In the water: acetonitrile (8:2,
v/v) system, when excited at 559 nm, the probe displayed a
significant emission peak at 528 nm. Upon the addition of
Zn2þ, a new strong emission peak at 608 nm was observed,
while the fluorescence at 528 nm was quenched, and the
solution visibly changed from green to pink, indicating a
significant FRET process. This process was supported by
fluorescence titration, mass spectrometry experiments, and
theoretical calculations, with a detection limit of 0.0289 lM.
In the excited state, the phenothiazine group of the donor
released a considerable amount of energy that was absorbed
by the rhodamine group in the ground state. After Zn2þ
was added, it combined with rhodamine, opening the helical
lacamide ring and extending the conjugated system, leading
to the quenching of the fluorescence of the phenothiazine
group. The rhodamine group used the absorbed energy to
undergo an electron transition and emitted pink fluores-
cence. Moreover, the probe was used to visualize Zn2þ in
living cells (Figure 41).
A series of new dendritic compounds probe 43–45, in
which the pyrene unit as the fluorophore and porphyrin as
the receptor, were synthesized by Rivera et al.[98] In the
THF solution, when the donor pyrene was excited at
344 nm, the residual pyrene monomer emission was
observed at 375 nm, followed by the emission of the porphy-
rin moiety, revealing the phenomenon of energy transfer
between pyrene to porphyrin. After the Zn2þ addition, Zn2þ
replaced the proton inside the probe, the probe showed a
red shift in the Soret absorption band and a blue shift in the
emission band and an energy transfer process from the
donor to the acceptor part, where the emission band of free
matrix porphyrin probe 45 was observed to shift from
653 nm to 603 nm. The calculated probe FRET efficiencies
were all located between 99.4 and 99.6% (Figure 42).
Most fluorescence sensors that possess FRET properties
are of the ratiometric type. Such fluorescent chemical sen-
sors usually emit double fluorescence. When the detected
20 J. WEN ET AL.
Figure 41. Sensing mechanism of probe 42 with Zn2þ.[97]
Figure 42. Sensing mechanism of probe 43–45 with Zn2þ.[98]
substance is identified, the intensity of one fluorescence
emission gradually decreases, and the intensity of the other
fluorescence emission gradually increases. A flexible linkage
between the acceptor and the donor dye is necessary for the
effectiveness of the fluorescence resonance energy transfer,
which is typically accomplished through carbon chains or
aromatic rings.[99]
Probes based on aggregation-induced emission
mechanism
Conventional fluorescent molecules usually exhibit strong
fluorescence in solution, but usually quenching in the solid-
state aggregation state occurs with a significant decrease in
fluorescence intensity. In contrast, aggregation-induced
emission (AIE) molecules exhibit significantly enhanced
fluorescence in the aggregated state, with fluorescence inten-
sity increasing as the molecules accumulate.[100] This phe-
nomenon is usually due to molecular aggregation, which
restricts degrees of freedom for rotation and vibration, mak-
ing non-radiative transitions dominant and leading to
increased fluorescence intensity. In the dispersed state, AIE
molecules usually present a non-radiative relaxation process,
in which the excited state energy is converted to the ground
state through vibration or non-radiative energy. However, in
the aggregated state, the non-radiative relaxation process is
prevented due to dense packing and limiting motion within
the molecule, thus converting the excited state energy to
photon energy by means of fluorescence emission.[35,101,102]
A new benzofuran-based fluorescent probe 46 was
designed by Diana et al.[103] In the TCE/hexane-diluted
solution, the solution gradually changed from colorless to a
visible red fluorescence due to the formation of emission
aggregation, verifying the AIE characteristics of the probe.
Subsequent fluorescence titration showed that in the TCE
solution, the probe displayed an emission peak at 533 nm.
Upon the addition of Zn2þ, the fluorescence of the zinc
complex was significantly enhanced, and the spectrum
shifted to 661 nm. When the probe interacted with zinc ions
or other alkali metal ions, only the presence of Zn2þ
resulted in a spectral redshift and visible fluorescence
enhancement, indicating the probe’s excellent selectivity for
Zn2þ. Based on the DFT method’s theoretical calculations,
the redshift of the fluorescence spectrum could be attributed
to the reduction of the HOMO-LUMO band gap of the zinc
complex, resulting from the Zn2þ and probe’s strong inter-
action, inducing electron cloud overlap of the electron-rich
region, conjugate extension, and promoting the redshift. The

enhanced fluorescence could be attributed to the closed-shell
Zn2þ locking the ligand and stabilizing the excited state via
the CHEF mechanism (Figure 43).
Naskar et al.[104] synthesized a novel Schiff base fluores-
cent chemical sensor probe 47 by condensation reaction. The
AIE characteristics of this probe were verified in a
DMSO/H2O mixture as the fluorescence intensity and wave-
length redshift of the probe were significantly enhanced with
an increase in water content, leading to a significant exten-
sion in the fluorescence lifetime. The probe had weak fluores-
cence at 513 nm under an excitation of 370 nm. After the
addition of Zn2þ, the fluorescence intensity was enhanced by
16 times, and the fluorescence color changed sharply from
colorless to yellow. The naked eye could detect Zn2þ with an
excellent detection limit of 0.0961 lM. The strong enhance-
ment of fluorescence with the increase of Zn2þ indicated that
Figure 43. Structure of probe 46.[103]
Figure 44. Sensing mechanism of probe 47 with Zn2þ.[104]
CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 21
Zn2þ triggered the AIEE (aggregation-induced emission
enhancement) effect in the probe. The quenching of the
fluorescence signal was mainly due to the orthogonality dis-
tortion of the p system caused by intramolecular rotation,
which resulted in the non-radiative relaxation process of
excited state energy. However, the binding of Zn2þ with the
probe inhibited the rotation of methylene benzodioxazole
and enhanced the flatness of the molecule. In the aggregation
state, the rotation of intramolecular bonds was restricted due
to the interaction between molecules, which enhanced the
flatness of the probe molecules and effectively inhibited the
electron effect, thus resulting in enhanced fluorescence. In
addition, the probe can be used for biological imaging of
HepG2 cells in vivo (Figure 44).
Wan et al.[105] synthesized two fluorescent probes, probe
48 and probe 49, based on helical difluorene. In DMF
22 J. WEN ET AL.
Figure 45. Structure of probe 48 and probe 49.[105]
solution, probe 48 displayed weak fluorescence emission.
However, with the slow addition of water, the fluorescence
emission of probe 48 began to increase, indicating the for-
mation of aggregates in the DMF/H2O mixed solution. The
inhibited intramolecular rotation in the aggregates blocked
the non-radiative relaxation channel and enhanced fluores-
cence. Probe 49 also demonstrated similar AIEE properties
in pure 1, 4-dioxane solution, confirming the AIEE behavior
of the two probes. Probe 48 in DMF/H2O (9/1, v/v) and
probe 49 in 1, 4-dioxane/water (13:7, v/v) exhibited very
weak fluorescence. However, upon the addition of Zn2þ, the
fluorescence intensity of probe 48 at 488 nm and probe 49
at 536 nm gradually increased, and the solution changed
from colorless to yellow. The detection limits for probe 48
and probe 49 were 0.3 lM and 0.063 lM, respectively. The
enhanced fluorescence was due to the AIEE activity of the
probe triggered by Zn2þ. The increase in Zn2þ concentra-
tion led to an increase in the average size of aggregates,
which consequently significantly increased fluorescence
intensity. Additionally, probe 48 was suitable for intracellu-
lar Zn2þ imaging, while probe 49 was suitable for two-pho-
ton fluorescence imaging of cells (Figure 45).
Molecules exhibiting AIE characteristics feature large
p-conjugate systems that suppress intramolecular rotation in
solution, leading to the fluorescence quenching. In molecu-
lar design, the conjugation of the aromatic ring and the
fluorescent group is avoided as far as possible, which helps
to avoid the self-aggregation or aggregation with other mole-
cules, and also contributes to the emission of molecular
fluorescence. Furthermore, the molecular configuration of
AIE molecules typically consists of a rigid backbone and a
luminescent group, and the intramolecular environment can
affect the fluorescence emission intensity and wavelength.
As a result, AIE molecules exhibit excellent photophysical
properties and find wide-ranging applications in fluorescent
sensors, biological imaging, and optoelectronic devices. As
far as we are aware, only a few fluorescent probes based on
AIE have been developed for detecting Zn2þ to date.[106–109]
Conclusions and perspectives
This paper reviews fluorescent probes for Zn2þ based on
different fluorescence sensing mechanisms, including photo-
induced electron transfer (PET), excited state intramolecular
proton transfer (ESIPT), intramolecular charge transfer
(ICT), fluorescence resonance energy transfer (FRET),
chelation-enhanced fluorescence (CHEF) and aggregation-
induced emission (AIE) mechanisms.
Through the overview, it was found that the most com-
monly used fluorophore in these zinc ion fluorescent probes
is the schiff base structure. This is primarily because this
structure can enhance the probe’s water solubility and its
tendency to bind to zinc ions. At the same time, fluorescent
probes designed based on fluorophores such as benzothia-
zole, naphthalimide, coumarin, pyrene, naphthalene, quin-
oline, coumarin and rhodamine are also being developed.
Additionally, it has been observed that a growing number of
researchers use quantum chemical tools to perform calcula-
tions on the structure of synthesized probes and zinc com-
plex structures. Through these computations, they can
comprehensively explore changes in the molecular structure,
electronic structure, and optical properties, to gain a reliable
and thorough understanding of the fluorescence mechanism
on a microscopic level. It can not only unify macroscopic
experiments and microscopic calculations, so that the
experimental conclusions are more convincing, but also ver-
ify and display the research results, providing strong support
for its application and promotion in academia and indus-
try.[110–112]
Despite significant progress in the development of Zn2þ
based fluorescent probes for sensing applications, there are
still some shortcomings in practical applications. Firstly, the
selectivity of fluorescent probes for Zn2þ is still limited in
current studies and is easily influenced by other metal ions
and molecular structures, resulting in less accurate detection
results. For example, Cd is located at group IIB, where Zn is
located, and has similar ionic radius and orbitals with Zn,
thus having similar spectral properties. Finding ways to pre-
vent Cd2þ interference in the selective detection of Zn2þ is
still a challenge. Secondly, most fluorescent probes exhibit
poor solubility in water and typically require the use of
organic solvents for detection, which restricts the practical
application of these probes. Thirdly, the small Stoke shift is
also a major problem for many fluorescent probes, with a
range of problems including shallow tissue penetration,
autofluorescence background interference, photobleaching
and photodamage in bioimaging applications. Lastly, a sig-
nificant amount of research is still focused on experimental
design and synthesis of new fluorescent chemical sensors,
while the sensing mechanisms are mostly based on empirical
evidence or inferred through experimental methods, many
of which have yet to be examined for accuracy, possibly
 CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 23

Table 1. Related parameters of the probes.

Emission
Probe Probe Sensing wavelength LOD Solvent Response
Representation Structure Mechanism (nm) (mM) pH Media Time Ref.
Probe 1 PET 668 0.21 6–8 Water 15 s [43]

Probe 2 PET 660 0.0048 6.50–8.53 CH3CN:water 30 s [44]

(1:1, v/v)

Probe 3 PET 451 250 / DMSO 60 s [45]

Probe 4 PET 489, 473 0.0236 6–12 ACN:H2O 10 s [46]

(8:2, v/v)

Probe 5 PET 438 0.0656 6.5 to 8.0 CH3CN: Water / [47]

(pH ¼ 7.4)

Probe 6 PET 428 0.107 6.5 to 8.0 CH3CN: Water / [47]

(pH ¼ 7.4)

Probe 7 PET 437, 455 / / MeCN / [48]

Probe 8 PET 490 / / Water: methanol / [49]

(1:1, v/v) (pH¼ 7.4)

Probe 9 PET 502–515 0.2206 6–10 Water: methanol / [49]

(1:1, v/v) (pH 7.4)

Probe 10 PET 450 0.0051 5–8 CH3CN:H2O (1:1, v/v) / [50]

Probe 11 PET 535–540 0.01925 6–14 HEPES buffer solution / [51]

(pH ¼ 7.4)

Probe 12 PET 560–570 0.0368 7–12 HEPES buffer solution / [52]

(pH ¼ 7.4)

(continued)
24 J. WEN ET AL.

Table 1. Continued.
Emission
Probe Probe Sensing wavelength LOD Solvent Response
Representation Structure Mechanism (nm) (mM) pH Media Time Ref.
Probe 13 PET 550 0.772 / HEPES buffer solution / [53]
(pH ¼ 7.4)

Probe 14 PET 550 4.25 / HEPES buffer solution / [54]

(pH ¼ 7.4)

Probe 15 ESIPT 423 0.1255 / methanol / [62]

Probe 16 ESIPT 406 0.623 / methanol / [62]

Probe 17 ESIPT 408 0.0243 / methanol / [62]

Probe 18 ESIPT 539 to 518 0.014 / acetonitrile / [63]

Probe 19 ESIPT 530 0.011 / H2O/DMSO / [64]

(90:10, v/v)

Probe 20 ESIPT 491, 534 0.00706 6–8.5 Water / [65]

Probe 21 ESIPT 450 0.35 / Ethanol solution 30 s [66]

(continued)
 CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 25

Table 1. Continued.
Emission
Probe Probe Sensing wavelength LOD Solvent Response
Representation Structure Mechanism (nm) (mM) pH Media Time Ref.
Probe 22 ESIPT 570 to 488 0.377 7–9 H2O/MeOH (2:3, v/v) <30 s [68]

Probe 23 ICT 550 / / DMSO:H2O (4:1, v/v) / [75]

Probe 24 ICT 550 / / DMSO:H2O (4:1, v/v) / [75]

Probe 25 ICT 469–489 0.6 / Acetonitrile solution / [76]

Probe 26 ICT 531 to 456 0.029 7–9 HEPES buffer: MeOH 150 s [77]
(3:2, v/v)

Probe 27 ICT 585 0.00018 6–12 HEPES buffer / [78]

Probe 28 ICT 557 0.00019 6–12 HEPES buffer / [78]

Probe 29 ICT 586 0.0311 5–8 DMSO:H2O (v/v, 1:9, 300 s [79]
HEPES, pH ¼ 7)

Probe 30 ICT 455 to 515 0.02–0.03 / Methanol: Buffer 2s [80]

(1:9, v/v,)

(continued)
26 J. WEN ET AL.

Table 1. Continued.
Emission
Probe Probe Sensing wavelength LOD Solvent Response
Representation Structure Mechanism (nm) (mM) pH Media Time Ref.
Probe 31 ICT 383 to 415 0.183 5–12 Water 240 s [81]

Probe 32 ICT 703 to 697 / / HEPES buffer / [82]

Probe 33 CHEF 404 0.03 2–12 DMSO/H2O (95:5, v/v) 25 s [86]

Probe 34 CHEF 660 / / Ethanol:buffer (3:7, v/v) 20 s [87]

Probe 35 CHEF 457 0.148 6–7 Ethanol:water (1:1, v/v) / [88]

Probe 36 CHEF 447 2.26 6–9 Bis-tris buffer / [89]

Probe 37 CHEF 452 1.12 6.0–7.6 Bis-tris buffer / [90]

Probe 38 CHEF 490 0.42 4–10 HEPES buffer / [91]

Probe 39 CHEF 493 0.27 7–10 DMSO:bistris buffer / [92]

Probe 40 CHEF 495 0.53 7–12 Bis-tris buffer:DMSO / [93]

(1:1, pH ¼ 7)

Probe 41 FRET 519 " 0.033 7–9 HEPES buffer 60 s [96]

362 # (pH ¼ 7.4)

(continued)
 CRITICAL REVIEWS IN ANALYTICAL CHEMISTRY 27

Table 1. Continued.
Emission
Probe Probe Sensing wavelength LOD Solvent Response
Representation Structure Mechanism (nm) (mM) pH Media Time Ref.
Probe 42 FRET 528 to 608 0.0289 5–14 Water: acetonitrile / [97]
(8: 2, v/v)

Probe 43 FRET 651 / / THF solution / [98]

Probe 44 FRET 652 / / THF solution / [98]

Probe 45 FRET 653 to 603 / / THF solution / [98]

Probe 46 AIE 533 to 661 / / TCE solution / [103]

Probe 47 AIE 513 0.0961 / DMSO/H2O (9:1, v/v) / [104]

HEPES buffer (pH ¼ 7.4)

Probe 48 AIE 488 0.3 6.1–10.5 DMF/H2O (9/1, v/v) / [105]

Probe 49 AIE 536 0.063 6–14 1, 4-dioxane/water / [105]

(13:7, v/v)

leading to misleading design and development of high-per-
forming fluorescent chemical sensors.
Based on these findings, future studies on the detection
of Zn2þ can be carried out in the following four aspects: (1)
Enhance selectivity: refine the molecular structure of the
probe through reasonable structural modification, adjust its
chemical affinity and selectivity toward zinc ions, decrease
its binding capability with other impurity ions, improve the
specificity of the probe toward zinc ions, and broaden the
probe’s application range. (2) Enhance water solubility:
introduce hydrophilic functional groups, such as amine
groups, benzimidazolyl groups, peptide groups, salicylic acid
28 J. WEN ET AL.
Table 2. Abbreviation list.
S/No. Full name
1 Photo-induced electron transfer
2 Excited state intramolecular proton transfer
3 Ground state intramolecular proton transfer
4 Intramolecular charge transfer
5 Fluorescence resonance energy transfer
6 Chelation-enhanced fluorescence
7 Aggregation-induced emission
8 Highest occupied molecular orbital
9 Lowest unoccupied molecular orbital
10 Limit of detection
11 Density functional theory
12 Circular dichroism spectrum
13 Photoacoustic imaging
14 Dimeric amine
groups, PEG chains, etc. into the zinc ion fluorescent probe
to improve water solubility of the probe. On the other hand,
the probe can be modified into water-soluble derivatives,
which can improve its stability and dispersion in water. For
example, fluorescent dyes can be modified with water-sol-
uble functional groups such as phosphate groups, sulfonate
groups or carboxyl groups. (3) Increase the Stoke shift:
introduce amino, radical, and nitrate groups in the opposite,
intermediate, or adjacent position to increase the resonance
structure of the probe molecule. This reduces the energy gap
between the ground and excited states, resulting in an
increased Stoke shift. Additionally, long-wavelength fluoro-
phores such as nitrogen-containing aromatics and macrocyc-
lic polyenes can be introduced to synthesize zinc ion probes
that exhibit near-infrared and infrared fluorescence emis-
sions. Examples of suitable fluorophores include naphtha-
lene, pyridine, anthracene, quinoline, porphyrin, bicyclic
ifosfluoridone, and others, which ultimately increase the
Stoke shift. (4) Integrate experiment and theory: use theoret-
ical calculations to investigate the interaction mechanism
between the fluorescent probe and zinc ions to better under-
stand the detection mechanism of the probe, and improve
its accuracy and reliability. In addition, by conducting sys-
tematic simulations and predictions of changes in the envir-
onment and structure of the zinc ion fluorescent probe, its
performance can be evaluated under different condi-
tions.[113] This method can quickly screen and optimize the
molecular structure and optical properties of the probe to
improve its selectivity, sensitivity, and anti-interference capa-
bilities. Such an approach can facilitate the swift develop-
ment of superior zinc ion fluorescent probes (Tables 1
and 2).
Author contributions
Conceptualization, J.W. and Y.X.; writing—original draft preparation,
J.W.; writing—review and editing, Y.X. Q.H. and S.D.; drawing figures,
Q.H. and A.S.; funding acquisition, Y.X. All authors have read and
agreed to the published version of the manuscript.
Conflicts of interest
The authors declare no conflict of interest.
Funding
Abbreviation
The author wishes to acknowledge the financial supports from the
PET
Natural Science Foundation of Hunan Province [No.2023JJ50167], the
ESIPT
GSIPT Scientific Research Fund of Hunan Provincial Education Department
ICT [No.22B0593] and the Hunan Provincial Innovation Foundation for
FRET Postgraduate [No.QL20220233].
CHEF
AIE
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