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1,8-Naphthalimide-based fluorescent
chemosensors: recent advances and perspectives
Cite this: J. Mater. Chem. C, 2020,
8, 13501
Hong-Qiang Dong,a Tai-Bao Wei, *a Xiao-Qiang Ma,a Qing-Yu Yang,a
Yun-Fei Zhang,a Yu-Jiao Sun,a Bing-Bing Shi,a Hong Yao, a You-Ming Zhang ab
and Qi Lin *a
1,8-Naphthalimide, as one of the classical dyes and fluorophores, has been widely used in analytical
Received 3rd August 2020, chemistry, materials chemistry, and biochemistry fields because of its excellent characteristic
Accepted 9th September 2020 photostability, good structural flexibility, high fluorescence quantum yield, and large Stokes shift. This
DOI: 10.1039/d0tc03681a review mainly focuses on 1,8-naphthalimide and its derivatives in ion detection, molecular recognition,
material applications, and bioimaging in the past five years. Simultaneously, we hope to develop more
rsc.li/materials-c powerful fluorescent chemosensors for broad and exciting applications in the future.
1. Introduction
More recently, the research on toxic ions and biological molecular
sensing,1–3 organic optoelectronic materials,4 high-performance
gels, and bioimaging applications have increasingly attracted the
attention of researchers.5–7 To date, great achievements have been
made in electrochemical detection,8 spectrophotometry,9 element
analysis,10 and chromatography.11,12 However, there are also a few
challenges in these methods, which include low accuracy, poor Fig. 1 (a) Chemical structure of 1,8-naphthalimide, (b) the application of
1,8-naphthalimide-based fluorescent chemosensors.
qualitative ability, expensive, and time-consuming. Fluorescent
techniques have attracted considerable research interests com-
pared with the above detection methods owing to their advantages
of low cost, fast response, noteworthy sensitivity, and simple We can see that the naphthalene ring acts as a p bridge, R1 is an
operation.13,14 Therefore, it has become the main detection electron-donating group (such as –NH2 and –OH), the imide
methods and has been widely used in biochemistry, chemistry, part acts as an electronic group constituting the D–p–A system,
medicine, and other fields.15–17 and 1,8-naphthalimide is also an electron-deficient system.27–30
1,8-Naphthalimide (NI), naphthalene diimide (NDI), pery- On the other hand, because of its outstanding light/thermal
lene bisimide (PBI), and their derivatives play a key role in the stability, it has become an important organic functional
field of fluorescent materials and dyes.18–21 In addition, the material.31–34 Moreover, the fluorescence colour will show
special structure of NI, NDI, and PBI endows them excellent changes accordingly when different substitutions are intro-
properties, high electron affinity, as well as good thermal duced at the 4-position base. At the same time, the above
stability and oxidation stability, which has led to their develop- mechanisms have been well-confirmed through theoretical
ment and application receiving widespread attention.22–24 calculations.35–37 Based on these characteristics, this scaffold
Naphthalimide, as the ‘‘simplest’’ molecule, has better water has found wide applications in the development of fluorescent
solubility than other molecules such as NDI and PBI. Therefore, chemosensors in the fields of molecular recognition, molecular
the study of naphthalimide derivatives has become a hot topic. imaging, bioorganic chemistry, analytical chemistry, materials
The structure of 1,8-naphthalimide is as shown in Fig. 1(a).25,26 chemistry, as well as in the biological and medical science
communities.38–40
However, naphthalimide-based fluorescent chemical sensors
a
Key laboratory of Polymer Materials of Gansu Province, College of Chemistry and
have not been reviewed. Although the research progress of
Chemical Engineering, Northwest Normal University, Lanzhou, Gansu, 730070,
P. R. China. E-mail: weitaibao@126.com, linqi2004@126.com
naphthalimide in ionic and biological aspects has been reviewed
b
Deputy Director-General of Gansu Natural Energy Research Institute, before,41,42 it has not been systematically summarized. In particular,
Renmin Road 23, Lanzhou, Gansu, 730070, P. R. China the rapid development of optoelectronic materials in recent years
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Fig. 2 Structure of the fluorescent chemosensor 1. Fig. 4 Structure of the fluorescent chemosensor 3.
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Fig. 7 (a) Proposed mechanism for the detection of Cu2+ ion, (b) fluores-
Fig. 5 Structure of the fluorescent chemosensor 4.
cence photographs of the sensor in the absence (left) and presence (right)
of Cu2+ in a dark-box ultraviolet analyzer when excited at 365 nm.
Fig. 6 (a) Proposed mechanism for the detection of Co2+ ion, (b) the
UV-vis absorption spectrum of sensor 5 (1 10 5 mol L 1) and upon the Fig. 8 (a) The structure of probe 7, (b) the ultraviolet photo of probe 7 and
addition of salts. with Cu2+, (c) the fluorescent photo of probe 7 and with Cu2+.
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Fig. 13 (a) The structure of sensor 14, (b) fluorescence emission data of
sensor 14 and different metal ions in solution.
Fig. 15 Illustration of the chloride-binding process of the aryl-triazole
foldamer 17 in the presence of anions.
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Fig. 17 (a) The proposed mechanism of 19 bonding with the F , (b) the Fig. 19 (a) The schematic representation of the assembly and disassembly
structures of the fluorescent sensor 19. of the sensor (22)-F, (b) fluorescence emission spectra of sensor 22 in
DMSO/H2O (7.4 : 2.6, v/v) solution in the presence of F and other anions.
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Fig. 32 (a) The sensing mechanism of 35 for GSTP1-1, (b) the synthesis
and proposed mechanism of probe 36.
Fig. 35 (a) The structure of sensor 39, (b) the fluorescence spectral of
Fig. 33 Design and synthesis of probe 37 for the detection of lysosomal probe 39 before and after the addition of MAO-A with emission color
H2Sn. changes, (c) the structure of sensor A.
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dyes, and organic pollutants can reach 99.8%. The high sensi-
tivity and broad-spectrum adsorption and separation perfor-
mance of 53-SPN are based on the multiple interaction sites
that we reasonably introduce. Therefore, this is a convenient
method for preparing supramolecular polymer network sponge
composite functional materials.
Soon after, they synthesized new guest molecules (TA) and
naphthalimide-functionalized pillar[5]arene host (54) to design
Fig. 44 (a) Chemical structure and photochromism of 55, (b) absorption
and construct a multifunctional sponge-like supramolecular spectra changes of 55 upon irradiation at 365 nm in cyclohexane solutions
polymer gel (Fig. 43).144 Interestingly, 54-G showed a spongy (5.0 10 5 M), (c) fluorescence spectra changes of 55 upon irradiation at
structure and strong AIE. In addition, 54-G also showed 365 nm in cyclohexane.
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Fig. 45 (a) The chemical structure of 56A and 56B, (b) photographs of
fluorescent aerogels depicting the fluorescence hydrochromism of 56A
and 56B based aerogels before and after being exposed to 90% RH taken
under 365 nm irradiation, (c) the UV-vis absorption and fluorescence Fig. 47 (a) Molecular structures of compounds 58(A–F), (b) PL spectra of
emission spectra of 56A and 56B aqueous solutions. luminogen 58(A–F) at different conditions.
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states. At the same time, the results of X-ray single crystal analysis
suggest that the distorted molecular conformation and the
absence of strong intermolecular forces lead to loosening of
the packing motifs, and the change in molecular packing is
responsible for the observed mechanical fluorescence effect. This
provides a valuable reference for the design of high-contrast
mechanical fluorescent materials based on 1,8-naphthalimide.
Cheng et al. (2019) used pyrene as the donor and 1,8- Fig. 49 Molecular structures of 60, (b) emission spectra of 60 in glycerol/
naphthalimide as the acceptor; a chiral D–A enantiomer (59A–B) water (85/15, v/v) mixture (left) and ethanol (right) recorded from 233 K to
was synthesized as a circularly polarized electroluminescence 323 K.
(CP-EL) emitter (Fig. 48).154 This chiral emitter exhibits good
thermal stability in the solid state (Td = 389 1C, Tg = 112 1C),
high fluorescence quantum yields (46.4/42.4%), and CPL-active
materials. Notably, the non-doped CP-OLEDs based on 59A/B
emitters can emit high green brightness CP-EL with gel signals
of +2.15 10 3 and 2.23 10 3, respectively. This work
provides a new perspective CP-EL emitter for the design of rigid
chiral structures.
Xu et al. (2016) reported a novel fluorescent intelligent unit
based on bisnaphthalimide 60 (Fig. 49),155 in which two frag-
ments of naphthalimide are conjugated at the 4-position by
twisting the single bonds. Taking advantage of the character-
istics of the bis-naphthalimide planar structure, 60 can be used
as a dual-channel rotor, outputting shorter emissions in the Fig. 50 (a) Synthetic TADF compound of 61A–Q, (b) visual representation
twisted state and longer emissions in the planar state. Due to of 61-N at various temperatures.
the limitation of the intramolecular rotation effect, 60 shows
strong emission characteristics in a high viscosity environment.
The longer and shorter emission in the aggregate is due to the Hudson et al. (2020) designed and synthesized naphthalimide-
synergistic effect of RIR and intramolecular planarization. The based red emission TADF acrylic monomer 61 (Fig. 50).156 When
probe produces a logarithmic response to different ratios of copolymerized with the host material by Cu(0)-reversible inactiva-
glycerol/water system viscosity. In addition, a very interesting tion radical polymerization (Cu(0)-RDRP), the polymer appears as
viscosity-dependent temperature response was also explored in a orange to deep red TADF, and the quantum yield in solution and
the fluorescence signal. We believe that this kind of fluorescent solid is as high as 58% and 31%, respectively. Utilizing this dual
sensor can distinguish the temperature-induced viscosity emission characteristic, the naphthalimide-isopropylacrylamide
change more effectively than that in other cases. dopant copolymerization produces blue fluorescence, preparing
a red to blue temperature-responsive polymer. These polymers
exhibit red TADF at room temperature and blue fluorescence at
70 1C, with a high ratio of 32.4% K fluorescence thermal response.
This system is expected to play a role in bioimaging, drug delivery,
and temperature sensing, thus further expanding the application
range of red TADF materials.
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Fig. 52 Chemical structures of the investigated photoinitiators 63(A–D), Fig. 54 Chemical structures of the studied naphthalimide derivatives
(b) UV-vis absorption spectra of 63(A–D) in acetonitrile. (65-A/G).
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Fig. 60 (a) The proposed mechanism of 71 for sensing H+, (b) fluores-
cence microscopy images of living HeLa cells co-stained with 71 (5 mM)
Fig. 62 (a) Molecular structures of 74, (b) co-localization of 74 and Lyso-
and LysoSensors Green DND-189 (1 mM).
Tracker Red in A549 cells.
Fig. 64 (a) Proposed mechanism of H2S release from probe 76 and HPLC
Fig. 61 (a) Molecular structures of 72 and 73, (b) co-localization real-time study of H2O2 induced HSD-B transformation, (b) confocal ratiometric
tracking of ROS production in living DU145 cells. fluorescence images on H9c2 cells.
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apoptosis process of cancer cells. In the presence of thioredoxin Over-expressed nitroreductase (NTR) is a common bio-
reductase (TrxR) in the mitochondria, a non-emitting com- marker of tumor hypoxia. Tang et al. (2020) designed and
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pound 73 is formed. This emission shutdown phenomenon synthesized a compound (74) of 1,8-naphthimide modified
allows the monitoring of the mitochondrial damage induced by with p-nitrobenzene, covalently attached to the side chain of
reactive oxygen species (ROS). As the dysfunctional mitochon- poly(fluorene-co-phenylene) (PFP) (Fig. 62).181 This compound
dria are cleared by the lysosome, 73 enters the lysosome and its can cause both FRET and PET to occur simultaneously. When
protonation leads to increased fluorescence. The results show NTR is present, the nitro group is reduced to an amino group,
that MPSE is very useful in elucidating the working mechanism causing the PET to be blocked. Therefore, the ratio is greatly
of theranostic-based optical apoptotic agents and it is hoped increased and the LOD was 19.7 ng mL 1. It is important that
that this mechanism will greatly promote the development of the fluorescence of the PFP backbone remains unchanged,
new cancer treatment methods. which allows it to be used as an internal reference. In addition,
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the ratio probe has high selectivity and low cytotoxicity, and can five years, which provides opportunities for promoting
realize NTR detection and hypoxia diagnosis in tumor cells. development in this field. In the past years, naphthalimide
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RNA is a product of cell metabolism and has a wide range of has become a powerful and highly adaptable platform.
functions, including protein synthesis, gene regulation, and We hope that this fluorophore has a bright future in the field
reaction catalysts. RNA mainly includes mRNA (mRNA), tRNA of fluorescence sensing. However, from the perspective of
(tRNA), and rRNA (rRNA). rRNA is the most abundant RNA. It is applications, there are several issues that need to be resolved:
produced in the nucleus and can be assembled with ribosomal (1) In the future, priority should be given to the development
proteins in all organisms to form ribosomes. However, these of fully biocompatible probes. This means that developing and
methods do not provide spatiotemporal information for three- designing water-soluble sensors is crucial. The above sensors
dimensional cells. Therefore, a method to display rRNA quickly basically exist in a large amount of organic solvents, which
and selectively in living cells is crucial. In 2019, Yi et al. should be solved.
developed a naphthalimide derivative probe 75 for the rapid (2) In terms of ion detection, most of the above reported
and selective detection of intracellular rRNA.182 Probe 75-A chemical sensors detect metal ions and toxic metal ions but few
showed a 32-fold increase in the fluorescence in response to of them detect alkali metals. For example, sodium ions have an
rRNA binding and showed good selectivity for rRNA relative to irreplaceable role in the adjustment of the osmotic pressure
DNA and other nucleic acid phosphate buffers at pH 7.2. More balance of human fluids. Therefore, it is necessary to develop a
importantly, 75-A has excellent nucleolus permeability and can sensor for alkali metal ion detection. In addition, in anion
be occupied by 4 different cell lines within 1 min. This is detection, the anion detection range should be expanded.
currently the fastest nucleolar dye (Fig. 63b). At the same time, (3) For applications in in vivo bioimaging, the naphthal-
the magnified nucleolar confocal laser micro-image and RNase imide scaffold should be altered to allow excitation and
digestion test showed that a pair of rRNA is highly selective, emission in the red and near infrared (NIR).
even for intracellular imaging. In addition, as a live cell probe, (4) Organic electroluminescence, temperament discolora-
due to the advantages of 75-A, including its water solubility, tion, and other materials play important roles in improving
excellent selectivity, remarkable photostability, biocompatibility, the photoelectric performance of light-emitting diodes. Organic
and peculiar cell permeability, we expect that this probe may small molecule emitters based on naphthalimide have attracted
provide an alternative tool for commercial rRNA staining. more and more attention due to their unique characteristics of
In 2020, He et al. introduced a new type of proportional electron extraction, rigid structure, and high fluorescence quan-
fluorescent H2S donor 76 (Fig. 64).183 The probe has the tum yield. In recent years, aromatic imide/amide semiconductors
following advantages: scavenges reactive oxygen species (more have been developed rapidly but there are few reports on their
specifically H2O2) while simultaneously generating H2S; application in OLEDs. Therefore, designing high-performance
provides ratio fluorescence that visualizes and quantifies H2S luminescent materials is a very meaningful study.163
release; specifically targets the mitochondria. This work pro- (5) In recent years, with the rapid development of
vides a new effective strategy for the design of fluorescent H2S Aggregation-induced emission (AIE) and Aggregation-induced
donors and provides strong evidence for the protective effect of emission enhancement (AIEE), the development of sensors with
cell models on myocardial ischemia-reperfusion injury. There AIE effect has become a research hot topic. Similarly, molecules
are other fluorescent chemosensors used in cell imaging and that develop naphthalimide and its derivatives in AIE and AIEE
medicine that have not been introduced one by one; see Table 2 chemiluminescence should be designed and studied.200
for details. Overall, we believe that there will be many fluorescent
chemical sensors based on naphthalimide in the near future,
and the structures and functions will be more novel and versatile.
6. Conclusion At the same time, we also hope that this review will promote
interest and new ideas in this emerging field of research.
1,8-Naphthalimide is a member of the family of classic dyes
and fluorophores. Due to its high fluorescence quantum yield
and easy modification property, especially the modifications of Conflicts of interest
different substituents (–NH2, –OH) at the 4-position, it shows
different fluorescence phenomena, which greatly expand its There are no conflicts to declare.
application. 1,8-Naphthalimide and its derivatives have been
widely used in chemical sensing, materials, biological imaging,
and other fields. Compared with other complex chemical Acknowledgements
molecules, it has the advantages of simplicity, high selectivity,
and high sensitivity, thus providing a broader research prospect This work was supported by the National Natural Science
for its application. Foundation of China (No. 21662031; 21661028; 21574104) and
This review summarizes the latest research progress in the Program for Chang jiang Scholars and Innovative Research
the field of ion detection, molecular recognition, material Team in University of Ministry of Education of China
application, biological imaging, and other aspects in the past (No. IRT15R56).
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