DOI: 10.1002/slct.
201601660 Full Papers
z Organic & Supramolecular Chemistry
Visual Sensing of Ag + Ions through Gelation of
Cholesterol- Appended Benzimidazole and Associated Ion
Conducting Behaviour
Kumaresh Ghosh,*[a] Santanu Panja,[a] and Subhratanu Bhattacharya[b]
Cholesterol-appended benzimidazole 1 has been synthesized.
The gelation ability of the compound 1 has been examined in
different solvents and it exhibits strong gelation with silver
perchlorate in DMF:H2O (1:1, v/v). Silver ion specific gelation in
DMF: H2O highlights the compound 1 as excellent visual
Introduction
Low molecular weight gelators (LMWG) are of enormous
interest, because of their potential applications in the field of
biomedicine, drug delivery, reaction catalysis, tissue engineer-
ing, water purifiers, optoelectronics etc.[1] Gels are dimension-
ally controlled viscoelastic semisolid materials formed by the
immobilisation of large volume of solvent into the three-
dimensional aggregation of LMWGs. The entrapment of solvent
molecules into the gel matrix is facilitated by the formation of
intermolecularly linked architectures of the gelators.
Supramolecular gelators interlink themselves through various
non-covalent interactions like hydrogen bonding, p-p stacking,
van der Waals interactions etc and set up cross-linked network
into which solvents on trapping result in gel formation.[2]
Molecules of this family bear different functional entities that
play crucial role to establish the non-covalent interactions for
self organization. Of different functional architectures, benzimi-
dazole motif receives attention[3] because of its duality in
hydrogen bonding. Moreover, p-p stacking between the
benzimidazole rings may also assist the molecules to form
aggregate.[3a,f,g]
During our ongoing effort in the area of supramolecular
chemistry research,[4] we have used the different simple
heterocylic motifs (e. g., pyridinium,[4a,b] benzimidazolium and
benzimidazole,[4c] triazole[4df] etc.) in devising some useful
molecular sensors for ionic substrates. In continuation, we
herein report a simple benzimidazole motif with cholesterol
[a] Prof. K. Ghosh, S. Panja
Department of Chemistry
University of Kalyani
Kalyani-741235 India
E-mail: ghosh_k2003@yahoo.co.in
[b] Dr. S. Bhattacharya
Department of Physics
University of Kalyani
Kalyani-741235 India
Supporting information for this article is available on the WWW under
http://dx.doi.org/10.1002/slct.201601660
ChemistrySelect 2017, 2, 959 – 966
detector of Ag + ions over a series of other metal ions.
Furthermore, silver-induced gel of 1 shows thermally activated
ionic conductivity due to the movement of Ag + ions within the
gel network.
phase 1 that behaves as nongelator without assistance of metal
ions. Among different metal ions, Ag + ion, a cation that is
actively exploited as antibacterial reagent,[5] is noted to tune
the self aggregation of 1 in DMF-H2O (1:1, v/v) and result in
formation of brown colored gel. This finding establishes the
compound 1 as an excellent detector of Ag + ion visually. In
solution, compound 1 further exhibited significant change in
emission upon successive addition of Ag + ions over the other
ions in DMF-H2O (1:1, v/v). Moreover, the Ag + -induced gel of 1
showed thermally activated ionic conductivity (hopping con-
ductivity).
Literature survey reveals that metal assisted supramolecular
assemblies are of special interest due to their applications in
catalysis, sensing, optics and magnetic field.[6] Moreover, metal
inclusion into LMWGs results in new functional hybrids with ion
conducting properties that can also be useful in super
capacitors, fuel cells, rechargeable batteries, solar cells etc.[7]
The fabrication of ion conducting gels are mainly concerned
with the formation of charge transfer domains by involving
non-conductive gelators. The use of metal organic frameworks
in this capacity is merely reported.[8]
It is to note that Ag + ion is used in the formation of self-
assembled gels and/or coordination polymers involving coordi-
nation between the Ag + ion and a donor heteroatom, such as
nitrogen or sulfur.[9] Besides these, alkene-Ag + interaction has
also been exploited by Smith et al., in the detection of Ag +
through sol-gel transition.[9j] Table 1S, in this regard, represents
in details the different gelator structures and their responsive-
ness to Ag + ions either through the disruption or formation of
gels in different solvent systems. In addition to the cited
examples in Table 1S, the present structure is synthetically
simple and excellent to detect Ag + ion giving formation of
stable gel which exhibits ionic conductivity as well.
959  2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Results and discussion
Synthesis
Compound 1 was synthesised according to the Scheme 1.
Initially cholesterol was converted to the chloride 2[4b] which on
Scheme 1. (i) Chloroacetyl chloride, pyridine, dry CH2Cl2, rt, 10 h; (ii) 4-
hydroxybenzaldehyde, CH3CN, K2CO3, reflux, 12 h; (iii) o-phenylenediamine,
DMSO, 90 0C, 10 h.
coupling with 4-hydroxybenzaldehyde in the presence of K2CO3
in CH3CN under refluxing condition introduced the compound
3. Oxidative condensation between o-phenylenediamine and
aldehyde 3 in dry DMSO at 90 8C afforded compound 1 in
appreciable yield. All the compounds were characterized by
usual spectroscopic techniques.
Gelation, morphology and rheological studies
Structural analysis of 1 as represented in Figure 1 reveals that
the benzimidazole motif being metal ion chelator is connected
Figure 1. Structure of compound 1.
to the cholesterol unit (hydrophobic part) via a rigid aromatic
spacer. In this structural feature, we believe that the benzimida-
zole moiety with conformational flexibility can assume different
alignments upon metal ion chelation into which the cholesterol
part will likely to be oriented to exert hydrophobic-hydro-
phobic interaction for establishing cross-linked network for
solvent trapping. It is mentionable that while compound 1
showed partial gelation in DMF: H2O (1:1, v/v), in other solvents
(Table 2S), it remained mostly either soluble or caused precip-
itation. However, addition of Ag + ions to the solution of 1 in
DMF: H2O (1:1, v/v) at room temperature brought instant
gelation. It is worthy to be mentioned that in presence of
2 equiv. amounts of Ag + ions, compound 1 at minimum
concentration of 11 mg/mL formed brown colored gel in DMF:
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Figure 2. Photograph showing the phase changes of 1 (15 mg/mL) in DMF:
H2O (1:1, v/v) in presence of 2 equiv. amounts of different metal ions
[c = 0.5 M in H2O as perchlorate salt] after 1 h.
H2O (1:1, v/v (Figure 2). Presence of Ag + ions below 2 equiv.
amounts makes the solution thick but did not stick on inversion
of vial.
We also investigated the effect of other metal ions in
gelation of 1 under similar conditions (Figure 2). Interestingly,
except Ag +, other metal ions under the study were silent in
bringing gelation of 1. These observations validate the selective
sensing of Ag + ions visually. In the gelation, there was no role
of the counter ion of Ag-salt. Under identical conditions, the
gelator 1 underwent gelation in the presence of AgNO3
(Figure 1S). The morphology of the gel was examined by SEM
images that showed layer by layer stacking of plate like
aggregates with voids for solvent trapping (Figs. 3a and 3b).
This is in sharp contrast to the morphology of the partial gel of
1 in the absence of Ag + ions in DMF:H2O (1:1, v/v) which
showed globular aggregates (Figs. 3c and 3d).
The interaction feature of 1 in presence of Ag + ion to form
gel was realized from comparison of FTIR spectra of 1 in its
amorphous and gel states (Figure 2S). The stretching for
benzimidazole -NH which appaeared at 3418 cm1 as sharp
signal in amorphous state, underwent small shifting in gel state
(~n = 2 cm1) with significant broadening (Figure 2S). Similarly,
stretching frequency for the ester carbonyl of 1 moved to the
lower region by 3 cm1 in gel state. Such small changes in FTIR
which cannot be ruled out are considered to be due to
involvement of the benzimidazole as well as the ester part in
the molecular packing during gelation. 1H-NMR study of 1 itself
and with equivalent amount of Ag + ion in CDCl3 exhibited very
small chemical shift change of the signals for aromatic protons.
This undoubtedly suggested the involvement of the benzimi-
dazole nitrogen in metal coordination (Figure 3S).
A shouldering at 341 nm in UV-vis spectrum of 1 in the sol
state suggested some degree of intermolecular association
through hydrogen bonding in the solution phase (Figure 4a).
Concentration variation UV-vis spectra of 1 in solution con-
firmed this. In dilute solution, the shouldering at 341 nm was
not found which confirmed the aggregation of 1 in concen-
trated solution. In fluorescence, the emission intensity of 1 at
~ 400 nm in concentrated solution moved to at 355 nm with
higher intensity when diluted (Figure 4b) and it was thus in
accordance with our presumption of aggregation. In gel state,
disappearance of this peak along with 6 nm bathochromic shift
of the absorption band towards 291 nm corroborates the
formation of new type of aggregates in gel matrix compare to
960  2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Figure 3. SEM images of xerogel of 1 with Ag + (a and b) and partial gel of 1 without Ag + (c and d) prepared from DMF: H2O (1:1, v/v) solvent system at
different scale bars.
the solution phase.[10] In fluorescence, gel state of 1 exhibited a
large red shifted emission with much lower intensity (Figure 4d)
which was probably associated to the aggregation-caused
quenching (ACQ) phenomena due to the nonradiative decay of
the fluorophore in the aggregated phase.[11] These experimental
observations altogether enabled us to suggest a probable
mode of interaction of the gelators with Ag + ions out of several
possibilities in forming the assembly (Figure 5).
To understand the formation mechanism of the Ag +
hydrogel and also to obtain the interlayer separation between
the stacked layers in the suggested mode in Figure 5, powder
X-ray diffraction (XRD) study of the dried Ag + gel of 1 (xerogel)
was performed. The XRD (Figure 6) pattern clearly indicates
that the self-assembled structure of the gelator results in from
both the van der Waals interaction between the cholesteryl
moieties and p-p interaction between the benzimidazoles. The
strong diffraction at 2q = 19.50 and 2q = 21.880 with corre-
sponding d-spacing of 4.56  and 4.13  are ascribed to the
van der Waals interactions between the alkyl residues of the
cholesterol parts[12] and the p-p interaction of the benzimida-
zole units[12,13] within the gel matrix, respectively. The peaks at
2q = 29.480 (d = 3.02 ), 32.50 (d = 2.75 ), 35.30 (d = 2.54 ) and
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38.920 (d = 2.31 ) corroborate the crystalline nature of the gel
fibers. Most of peaks with d- spacing lying within the range of
2.1  to 2.85  highlight the different bond lengths between
Ag (I) and the nitrogen of the benzimidazole units, depending
upon their mode of interaction within the matrix.[14] However,
the sharp diffraction peak at 2q = 35.30 designates the bond
length between the Ag(I) and oxygen atom of ester carbonyl.[15]
The diffraction peak at 2q = 32.50 signifies the hydrogen
bonding present in the network involving either ester carbonyl
or benzimidazole -NH with water used in the gelation.[12]
It is important to be mentioned that during recording of
UV-vis spectrum of the gel no absorbance at ~ 400 nm to
450 nm as plasmon peak for silver nanoparticles was observed.
This corroborated that Ag + - induced gelation of 1 is not
associated with the formation of Ag nanoparticles in the gel
matrix. Some particles in the SEM image in Figure 3 which may
lead to query in this aspect is therefore ruled out in our case.
The viscoelastic properties of the metallogel of 1 were
examined by rheology experiments, in which the variation of
dynamic storage modulus G’ and corresponding loss modulus
G’’ were measured as a functions of strain and frequency
(Figure 7). A nonlinear response of both G’ and G’’ were
961  2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
 Full Papers

Figure 4. Concentration dependent (a) absorption and (b) emission spectra of 1 in DMF: H2O (1:1, v/v); Comparison of (c) normalized UV-vis and (d)
fluorescence spectra (lex = 285 nm) of 1 in the sol and gel states.

Figure 5. Suggested mode of interaction of 1 in gel state.

Figure 6. X-ray diffractogram of the dried Ag + gel of 1.

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Figure 7. Rheology experiment of the Ag + gel of 1 in DMF: H2O (1:1, v/v).
Figure 8. (a) Variation of gel melting temperature (Tg) of 1 with gelator concentration in DMF: H2O (1:1, v/v, with 2 equiv. amounts of Ag +); (b) Chemical
responsiveness of the metallogel of 1 [15 mg/ mL in DMF: H2O (1:1, v/v) with 2 equiv. of Ag + ] upon successive addition of 2 equiv. amounts of Cl (c = 0.2 M)
and Ag + (c = 0.2 M) ions.
observed with the applied strain amplitude at a fixed frequency
(w = 10 rad/s). With gradual increase in the applied stress both
G’ and G’’ were deviated from linearity and beyond a certain
stress of 34 Pa (yield stress) a sharp fall of both G’ and G’’ values
were observed indicating that the gel started to collapse. In
frequency sweep experiment at a fixed strain of 1 %, both G’
and G’’ were frequency invariant over the entire range studied
and the values of G’ were more than 5 times higher than those
of G’’ at any frequency, signifying dominant elastic character of
the metallogel.
Supramolecular gels usually display thermal induced gel to
sol transition due to crumple of intermolecular forces respon-
sible for gelation. With increase in temperature, the metallogel
of 1 at mgc started to disintegrate at 54 oC (Tgel). A linear
increase in gel melting temperature was also observed with
increase in gelator concentration (Figure 8a). However, the
ChemistrySelect 2017, 2, 959 – 966
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metallogel was not thermo reversible probably due to the poor
solubility of the 1-Ag + aggregates in that solvent system. Such
kind of gel-sol transition of 1 was also observed in presence of
Cl ions at room temperature (Figure 8b). Addition of 2 equiv.
amounts of Cl ions resulted in scavenging of Ag + ions from
the gel medium as AgCl and caused rapid destruction of the
gel within 15 mins. Further addition of Ag + ions influenced the
ligand 1 to reorganize for gelation slowly (time taken: ~ 1 h).
During recovery process, the color of the gel changed to light
brown rather than deep brown.
Metal ion binding in solution phase
In an effort to understand the solution phase interactions of 1
with the metal ions, UV-vis and fluorescence titrations of 1 (c =
2.50 x 105 M) with different metal ions (taken as perchlorate
963  2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

salts, c = 1.0 x 103 M) were performed in DMF: H2O (1:1, v/v). In
fluorescence, while compound 1 showed measurable interac-
tion with Ag + and Cu2 + ions, other metal ions perturbed the
emission weakly (Figure 4S). Figure 9a, in this regard, represents
Full Papers
323 K with temperature steps of 5 K. For measurements, the
sample was placed between two parallel steel electrodes with a
Teflon ring spacer in a constant-volume cylindrical cell. The
temperature was controlled using Eurotherm temperature
controller and temperature constancy of  0.2 K was achieved
in the entire range of measurements. To examine the arbitrary
errors related to the changes in the environmental conditions
and contact etc., the experiment was repeated by several times.
The deviations or errors found in the frequency dependent
conductance and capacitance values were less than 3 % with
identical nature at different temperatures.
The frequency dependence of the real part of the complex
ac conductivity of the gel at different temperatures, as
estimated from the measured frequency dependent capaci-
tance and conductance is displayed in Figure 10 with 10 K

Figure 9. (a) Change in fluorescence ratio [I–I0/I0] of 1 at 370 nm

(lex = 285 nm) upon addition of 3 equiv. amounts of a different metal ions
and (b) fluorescence titration of 1 with Ag + (c = 1.0 x 103 M) [conc. of
1 = 2.50 x 103 M and conc. of metal = c = 1.0 x 103 M in DMF: H2O (1:1, v/v)].

the change in fluorescence ratio of 1 at 370 nm in presence of

3 equiv. amounts of different metal ions. Initially, upon
excitation at 285 nm, compound 1 showed two distinct
emission peaks at 355 nm and 370 nm. Upon gradual addition
of Ag + ions, emission intensities of these peaks underwent
significant quenching without producing any other change in
the emission spectra (Figure 9b). The emission titration data for
1 with Ag + was analysed to understand the strength of
interaction and the association constant was calculated as 1.79
x 104 M1 from Benesi-Hildebrand linear plot,[16] characteristic of
1:1 complexation (Figure 5S). In this event, the detection limit[17]
for Ag + was estimated to be 4.31x105 M (Figure 6S). Interfer-
ence study at 370 nm showed selectivity of 1 towards Ag + ions
while other metal ions undertaken in the study were found to
be non-interfering (Figure 7S). The silver specific interaction of
1 in solution was also observed in ground state. In UV-vis
titration, in presence of Ag + ions, the intensity of the peak at
285 nm was decreased considerably with a red shift of 6 nm
(Figure 8S). In case of other metal ions, the change in Figure 10. Frequency dependent real part of the complex conductivity of the
Ag-gel of 1 at different temperature (10 K interval). Inset shows the
absorbance of 1 was negligible (Figure 8S). Carful study reveals temperature variations of dc conductivity. Solid line is the best fits to Eq. 1..
that no absorption in between 400 nm to 450 nm for plasmon
peak of silver nanoparticles was noticed during UV-vis titration.
This was also true even on keeping of the solution of 1
containing Ag + ions for longer time or irradiation of solution temperature step. In the low frequency region, the real
with sunlight (Figure 9S). conductivity decreases with frequency. This behaviour corre-
sponds to the electrode polarization (EP) effect, which occurs
due to accumulation of space charges at the electrolyte-
Ionic conductivity study
electrode interface.[18] Above a certain frequency, the conductiv-
The Ag + - gel exhibited ionic conductivity in its gel state that ity is observed to be frequency independent within the
varies with temperature. The ionic conductivity of the gel was measured frequency range and this is attributed to the
measured by means of impedance spectroscopy (Hioki 3532– macroscopic dc conductivity of the gel. The inset of Figure 8
50 LCR Hi-Tester) in the frequency range of 40 Hz to 200 kHz at depicts the temperature dependence of the estimated dc
an amplitude of 0.5 V, within the temperature range of 253 to conductivity (sdc) of the gel. The non-Arrhenius temperature

ChemistrySelect 2017, 2, 959 – 966 964  2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

dependence of the conductivity is suitably explained by the
modified Vogel  Tammann  Fulcher (VTF) equation.[19,20]
sdc ¼ s0 exp ½BT0 =ðT-T0 Þ ð1Þ
where s0 is the pre-factor, B = (constant)(Dm/K) is the
fragility parameter with K and Dm that relate to the density of
minima on the potential surface and the barrier heights
separating the minima, respectively.[20] The characteristic Vogel
temperature ‘T0’ is the characteristic temperature, where the
molecular motions cease.[19] The solid line in the inset of
Figure 9 represents the non-linear least square fitting of the
conductivity data to Eq. (1) with the fitting parameters s0 =
0.38 Scm1, B = 3.13 and To = 164 K. Considerably higher value
of the fragility parameter and also the rheology observations
indicate the existance of higly amorphous and disordered
rubbery state within the gel that promotes the thermally
activated conduction of Ag + ions within it.
Conclusion
In conclusion, gelation propensity of cholesterol appended
benzimidazole 1 has been evaluated using different transition
metal ions. Only the gelator 1 shows gelation in DMF: H2O (1:1,
v/v) in the presence of Ag + ions and validates the naked eye
detection of Ag + ion over a series of other metal ions. The
solution phase interaction study of 1 in fluorescence in DMF: H2
O (1:1, v/v) also reveals the selectivity for Ag + ions. As an
application, Ag + -induced metallogel has been explored in ion
conductivity study. Thus gelator 1 is a new insight in
construction of conducting supramolecular gels where the
metal ions are responsible for the formation of a disordered
rubbery gel matrix, suitable for ion migration under an applied
ac electric field.
Acknowledgments
KG thanks DST [755 (Sanc.)/ST/P/S & T/4G-3/2014, dated 27. 11.
2014], West Bengal, for providing financial assistance. SP thanks
CSIR, New Delhi, India for a fellowship. KG also thanks Prof. P.
Dastidar, IACS, Kolkata for rheological study. SB thanks DST,
New Delhi, for providing the instrumental facilities in the
Department of Physics under DST-FIST scheme.
Conflict of Interest
The authors declare no conflict of interest.
+ Wang, G. Zhang, D. Zhang, D. Zhu, B. Z. Tang, J. Mater. Chem. 2010, 20,
Keywords: Ag sensing · Cholesterol-linked benzimidazole ·
Fluorescence · Ionic conductivity · Supramolecular gel
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