Sensors and Actuators B 230 (2016) 40–45

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Sensors and Actuators B: Chemical

journal homepage: www.elsevier.com/locate/snb

A multi-responsive cyanine-based colorimetric chemosensor

containing dipicolylamine moieties for the detection of Zn(II) and
Cu(II) ions
Ying Hu a , Jun Yin b,∗∗ , Juyoung Yoon a,∗
a
Department of Chemistry and Nano Science, Ewha Womans University, Seoul 120-750, Republic of Korea
b
Key Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, PR
China

a r t i c l e i n f o a b s t r a c t

Article history: A cyanine-based chemosensor containing dipicolylamine moieties is reported and its structure is well-
Received 22 November 2015 defined. Investigation on the optical property shows it is pH-independent. Acidic medium can induce
Received in revised form 5 February 2016 the color change from azure to dark blue while it presents the green in the alkaline condition (pH 10)
Accepted 10 February 2016
in comparison to the neutral condition. More, owing to the introduction of dipicolylamine units, this
Available online 11 February 2016
chemosensor can be used as a colorimetric indicator for Zn(II) and Cu(II) ions along with color change
from green to bright blue. Especially, its copper complex has a capability of determining the sulfide anion
Keywords:
(S2− ) with high selectivity, and as a consequence, the color of solution turns back to the green. This work
Cyanine
Colorimetric chemosensor
provides a promising indicator for the analysis of multi species.
pH sensor © 2016 Published by Elsevier B.V.
Copper sensor
Sulfide sensor

1. Introduction
In recent years, chemosensors based on optical response
have attracted the attention of many researchers [1]. In gen-
eral, there are two types of chemosensors that produce optical
responses. One type of chemosensor is colorimetric, producing
color changes that are directly visible to the naked eye. The other
chemosensor produces fluorescence-responses, which are based on
emission changes. Over the past several years, numerous promis-
ing chemosensors with different fluorophores have been developed
and used in the detection of cations, anions, bioactive species, etc.
[2].
Among different types of fluorescent dyes, indocyanine green
is one of the most classical dyes, producing fluorescence in the
near infrared region of the spectrum. Therefore, it has been widely
used in fluorescent probes. It is also used for bioimaging of cells
and tissues, because it has weak background interference, caus-
ing low photo-damage [3–7]. Furthermore, it penetrates deeply
into the tissues [3]. In general, most fluorescent dyes absorb UV
light of a shorter wavelength. However, cyanine and its derivatives
usually exhibit a deeper color because they absorb UV light of a
longer wavelength, which is usually over 700 nm. Therefore, they
are green or blue in color [5]. Although the cyanine-based sensors
exhibit a fluorescence-response, it is challenging to develop col-
orimetric chemosensors with cyanine moiety. It is a well-known
fact that color change is always associated with the conjugation of
␲-electrons. In our previous study, we used the strategy of con-
jugation to develop a colorimetric fluorescent probe of thiols [6].
Recently, we have found that cyanine containing dipicolylamine
ligand can serve as a colorimetric fluorescent probe, which can be
used for detecting zinc in cells and in vivo. This is because there is
rearrangement of conjugated system in this ligand [7].
In this study, we developed a colorimetric cyanine-based
chemosensor containing dipicolylamine moieties; it was used to
detect Cu(II) and Zn(II) ions as it produced color changes, which
were visible to naked eyes. Interestingly, the copper complex had
the capability of detecting sulfide ions. Furthermore, the introduc-
tion of pyridine units ensured that the sensor is sensitive to pH.
2. Experimental
2.1. Materials and equipment

Unless otherwise stated, all materials were obtained from com-

∗ Corresponding author. Fax: +82 2 3277 2384. mercial suppliers and were used without further purification. Thin
∗∗ Corresponding author. Fax: +86 27 6786 7725. layer chromatography (TLC) was carried out using Merck 60 F254
E-mail addresses: yinj@mail.ccnu.edu.cn (J. Yin), jyoon@ewha.ac.kr (J. Yoon). plates with a thickness of 0.25 mm. 1 H NMR and 13 C NMR spectra

http://dx.doi.org/10.1016/j.snb.2016.02.040
0925-4005/© 2016 Published by Elsevier B.V.
 Y. Hu et al. / Sensors and Actuators B 230 (2016) 40–45 41

Fig. 1. The structure of chemosensor 1, and its response to pH and metal ions. (For interpretation of the references to color in the text, the reader is referred to the web
version of this article.)

Scheme 1. The synthetic route of probe 1.

were recorded using Bruker 300 MHz spectrometer. The chemi-

cal shifts are given in ppm and the coupling constants (J) in Hz.
The mass spectra were obtained using a JMS-HX 110A/110A Tan-
dem Mass Spectrometer (JEOL). The UV absorption spectra were
obtained on a UVIKON 933 Double Beam UV/VIS Spectrometer.

2.2. Synthesis

2.2.1. Probe 1
To a solution of IR-780 iodide (334 mg, 0.5 mm) in dry
DMF (5 mL), compound 3 (266 mg, 0.5 mm) was added. The
mixture was stirred for 24 h at 90 ◦ C under nitrogen atmo-
sphere. After cooling to room temperature, the solvent was
removed. The crude product was purified by column chro-
matography (eluent: MeOH/dichloromethane 1:20), affording the
desired product. Yield, 21%. 1 H NMR (300 MHz, CDCl3 ) ı 0.91 (t,
J = 7.8 Hz, 6H, NH(CH2 )CH3 ), 1.21 (s, 12H, −CH3 ), 1.65–1.73 (m,
4H, NHCH2 CH2 CH3 ), 1.85 (t, J = 6.0 Hz, 2H, cyclohexyl H), 2.42 (t,
J = 6.3 Hz, 4H, cyclo-hexyl H), 3.14 (m, 8H, NHCH2 CH2 CH3 and
phenyl–CH2 ), 3.82 (s, 8H, pyridine–CH2− ), 5.63 (d, J = 13.5 Hz, 2H,
alkene-H), 6.82 (d, J = 7.8 Hz, 2H, Ph-H), 6.89–6.98 (m, 4H, Ph-H),
7.09 (t, J = 5.1 Hz, 4H, pyridine–H), 7.18 (t, 2H, J = 8.4 Hz, Ph-H),
7.37 (s, 2H, phenol–H), 7.54 (d, J = 7.8 Hz, 4H, pyridine–H), 7.61 (t,
J = 7.5 Hz, 4H, pyridine–H), 7.98 (d, J = 13.5 Hz, 2H, alkene–H), 8.47
(m, 5H, pyridine–H and NH); 13 C NMR (75 MHz, CDCl3 ) ı 11.91,
20.52, 22.02, 28.66, 45.57, 48.21, 54.84, 59.68, 96.78, 109.31, 120.59,
122.07, 122.39, 123.28, 128.27, 137.10, 140.38, 142.31, 143.01,
149.02, 151.77, 158.76, 161.45,169.31; FAB-MS for [C68H76N9O-
I]+ calcd for 1034.62, found 1034.7.

2.3. UV absorption studies

Fig. 2. The pH-dependent absorption spectra of probe 1 (10 uM), which is dissolved
Stock solutions of probe 1 (1 mM) were prepared in DMSO. Metal in a buffer solution containing 1% DMSO (A); (B) the color changes of probe 1 at pH
ions stock solutions (10 mM) of the perchlorate salts of Ag+ , Ca2+ , 4, 7, and 10, respectively. (For interpretation of the references to color in the text,
Cd2+ , Co2+ , Cs+ , Cr3+ , Cu2+ , Fe2+ , Fe3+ , Sr2+ , Hg2+ , K+ , Li+ , Mg2+ , Mn2+ , the reader is referred to the web version of this article.)
Na+ , Ni2+ , Pb2+ and Zn2+ ions in distilled water were prepared.
Stock solutions (10 mM) of the anions stock solutions of the sodium
salts of ppi, PO4 3− , HPO4 2− , F− , Cl− , Br− , I− , S2− , CH3 COO− , CN− ,
42 Y. Hu et al. / Sensors and Actuators B 230 (2016) 40–45

Fig. 3. (A) The color changes of probe 1 in the presence of Zn2+ and Cu2+ ions; (B)
absorbance changes of probe 1 (5 ␮M) with different concentrations of Zn2+ (0–3.0
eq.) in HEPES (0.1 M, pH 7.4) containing 1% DMSO; (C) absorbance changes of probe
Fig. 4. (A) The color changes of 1-Cu complex in the presence of S2− ions; (B) using
1 (5 ␮M) with different concentration of Cu2+ (0–3.0 eq.) in HEPES (0.1 M, pH 7.4)
probe 1 (5 ␮M) complex with Cu2+ (5 eq.), we obtained the absorbance spectra for
containing 1% DMSO. (For interpretation of the references to color in the text, the
various anions, and energy molecules, such as ATP, ADP, AMP (10 eq.) in HEPES
reader is referred to the web version of this article.)
(10 mM, pH 7.4,) containing 1% DMSO; (C) the change in the absorbance of probe 1
(5 ␮M) complex with Cu2+ (2 eq.) using various concentration of S2− (0–10 eq.) in
HEPES (10 mM, pH 7.4,) containing 1% DMSO. (For interpretation of the references
N3 − , SCN− , NO3 − , HSO4 − were prepared in twice-distilled water. to color in the text, the reader is referred to the web version of this article.)
Stock solutions of ATP, ADP, AMP (10 mM) were prepared in twice-
distilled water.
The test solutions were prepared by placing 30 ␮L of the probe 3. Results and discussion
stock solution into a test tube, adding an appropriate aliquot of each
metal stock solution, and diluting these stock solutions to 3 mL with 3.1. Synthesis
HEPES buffer (10 mM, pH 7.4) and 1% DMSO. For all of the mea-
surements of UV/Vis titration experiments were performed using The cyanine-based chemosensor 1 was synthesized according
10 ␮M of 1 and 1-Cu2+ in 1.0% DMSO aqueous solution (pH 7.4, to the route outlined in Scheme 1. In this method [8], 4-acetamino
10 mM HEPES buffer) with varying concentrations of the sodium phenol (2) was used as the starting material. It reacted with dipi-
salts at room temperature. colylamine (DPA) to produce the desired ligand 3, which was
 Y. Hu et al. / Sensors and Actuators B 230 (2016) 40–45 43

Fig. 5. Frontier molecular orbital profiles and optimized structures based on TD-DFT (B3LYP/6-31G*) calculations of probe 1.

then treated with cyanine IR-780 in anhydrous dimethylformamide
(DMF) under nitrogen atmosphere. Thus, we produced a solid that
was bright blue in color. The pure form of probe 1 was obtained by
column chromatography; the yield of this reaction was 21% Fig. 1.
3.2. Spectral studies of probe 1
The probe 1 can be used to evaluate the response toward pH
as it contains polypyridine and amino groups [1d,9]. However, we
first investigated the optical behavior of probe 1 under acidic con-
dition. As shown in Fig. 2(A), probe 1 (10 ␮M) produces a broad
absorption band in the near infrared region of the spectrum; the
band shows maximum absorption at 742 nm; this band was pro-
duced when probe 1 was dissolved in a buffer solution containing
1% dimethyl sulfoxide (DMSO). The buffer solution had a neutral pH.
But, with the enhancement of acidity, we observed that there was
an increase in the absorption. As shown in Fig. 2(B), the color of the
solution changed from green to bright blue. In contrast, in an alkali
medium, probe 1 undergoes ratiometric color changes, because the
wavelength of absorption decreases and moves toward the near-
infrared region; maximum absorption is observed at 450 nm. As
shown in Fig. 2(B), the solution turns bright yellow in color.
Subsequently, we determined the response of probe 1 toward
various metal ions. As shown in Fig. 3(A), only Zn(II) and Cu(II)
ions could induce an obvious color change from green to blue
(also see Fig. S4 in Supporting information). We determined the
absorbance of probe 1 (5 ␮M) while titrating it against Zn2+ and
Cu2+ (0–3 eq.) ions, which were dissolved in 4-(2-hydroxyethyl)-
1-piperazineethanesulfonic acid (HEPES) (0.1 M, pH 7.4) containing
1% DMSO. As shown in Fig. 3(B), the Zn2+ ions clearly increased the
absorbance with an increasing concentration of Zn2+ . A blue shift of
about 25 nm was observed simultaneously. In this titration, we also
44 Y. Hu et al. / Sensors and Actuators B 230 (2016) 40–45
observed that Cu2+ (0–3 eq.) was added gradually to the solution
of probe 1 (5 ␮M) under same conditions, there was a clear shift
blue shift and the absorbance increased (Fig. 3(C)). In the structure
of probe 1, there are two DPA units, indicating that it can bind with
two equivalents of metal ions. The experimental results from Job
Plots confirmed that probe 1 can form complexes in the ratio of
1:2 with Zn2+ and Cu2+ . Therefore, probe 1 has very strong binding
affinity to Zn2+ and Cu2+ , respectively (Figs. S5 and S6 in Supporting
information). Furthermore, it is worth mentioning that probe 1 has
lower detection limits for Zn2+ and Cu2+ ions (Fig. S7 in Supporting
information).
Since metal complexes can be used to detect anions [10], we
used Zn2+ and Cu2+ complexes of probe 1 to detect various anions
in the second experiment. We investigated the response of zinc(II)
complex 1-Zn to detect anions and nucleoside phosphates, such
as ATP, ADP, and AMP. There were no obvious changes in the
absorbance spectra (Fig. S8 in Supporting information). However,
as shown in Fig. 4(A), the copper(II) complex 1-Cu of probe 1 under-
went a color change from blue to green when sulfide anion (S2− )
was added to HEPES (10 mM, pH 7.4) containing 1% DMSO. The
UV–vis absorption spectra illustrated that the complex 1-Cu had
high selectivity for S2− ions under identical conditions. By carrying
out further titration, we found that the UV–vis absorption spectrum
gradually undergoes a red-shift due to the addition of S2− (0–10
eq.). There was also decrease in the intensity of absorption. Unlike
the binding process of probe 1 with Cu2+ ion, UV–vis absorption
of probe 1 was a completely reversible process. Furthermore, 1-Cu
complex had a lower detection limit for S2− (Fig. S9 in Supporting
information). Since sulfide anion is used for the conversion into sul-
fur and sulfuric acid and exposure to a high level of sulfide anions
is known to cause unconsciousness and respiratory paralysis [11],
optical detections of sulfide anions have been actively studied [12].
Our current results also indicated that the Cu(II) complex of probe
1 is a highly selective chemosensor that can be used to detect the
S2− ions in aqueous solution.
We performed a more detailed analysis of the structure and
electron density of probe 1 in order to gain an insight into its
optical behavior. Therefore, we used the time-dependent density
functional theory (TD-DFT) to optimize the structure of probe 1
at the B3LYP/6-31G* level using a suite of Gaussian 09 programs.
As shown in Fig. 5, two DPA units were symmetrically distributed
into the two sides of a phenol group, while a cyanine fluorophore
had a twisted backbone with conjugation. In the frontier profiles
of molecular orbitals, the electron density in the HOMO orbital of
probe 1 was mainly associated with a part of the phenolic group
and one of the DPA units. In the LUMO orbital of probe 1, the elec-
trons were delocalized on the polyene unit, which extends onto
cyanine fluorophore. Consequently, an intense S0 → S3 transition
was observed in probe 1, with the highest oscillator strength being
1.4176. The transition mainly occurred from HOMO-1 → LUMO (in
Table S1). We found that the molecular orbitals were also involved
in a few electronic transitions. The result indicated that there was
no intramolecular charge transfer in this system.
4. Conclusion
In summary, we have reported a cyanine-based chemosensor,
which contained two dipicolylamine units. Owing to its optical
property, its color changed from green to dark blue in an acidic
medium. In an alkaline medium, the chemosensor became yellow
in color. Moreover, Zn(II) and Cu(II) ions could also change the color
of the probe from green to blue. Furthermore, the Cu(II) complex
of the chemosensor could bind with anions, and it showed a high
selectivity for sulfide anions. This research study proves that the
probe can be used as a highly selective chemosensor to detect the
S2− ions in an aqueous medium.
Acknowledgments
This research study was supported by a grant from the National
Creative Research Initiative Program of the National Research Foun-
dation of Korea (NRF), which is funded by the Korean government
(MSIP) (No. 2012R1A3A2048814). We also acknowledge the finan-
cial support from National Natural Science Foundation of China
(21402057). Mass spectral data were obtained from the Korea Basic
Science Institute (Daegu) on a Jeol JMS 700 high resolution mass
spectrometer.
Appendix A. Supplementary data
Supplementary data associated with this article can be found, in
the online version, at http://dx.doi.org/10.1016/j.snb.2016.02.040.
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Biographies
Ying Hu received her Bachelor degree in Applied Chemistry (Fine Chemical Engi-
neering) from East China University of Science and Technology (ECUST, Shanghai) in
2011. She is currently on Ph.D. studies under the supervision of Prof. Juyoung Yoon
in the Department of Chemistry and Nano Science at Ewha Womans University. Her
research interests include fluorescent chemosensors and molecular recognition.
Prof. JunYin was born in Hubei province, P. R. China, in 1981. He received his Bache-
lor’s degree in 2002 and Ph.D. degree in 2007 from Central China Normal University
(CCNU). He began his postdoctoral research at National University of Singapore
before he joined the College of Chemistry, CCNU in 2010. He is now an associate
professor at CCNU. His research interests focus on functional supramolecular self-
assembly, fluorescent sensors and biological functional materials.
Prof. Juyoung Yoon is the full professor at the Department of Chemistry-Nano Sci-
ence, Ewha Womans University, Seoul, Korea. He received his Ph.D. (1994) from The
Ohio State University. His research interests include investigations of fluorescent
chemosensors, molecular recognition and organic functioinal materials.