A Turn-On Fluorescence Chemosensor for Cyanide in Aqueous Media Based on a Nucleophilic Addition Reaction

Article abstract of DOI:10.1002/cjoc.201600811

We synthesized a new cyanide (CN^?) chemosensor CX based on a nucleophilic addition reaction prompted by cyanide ion, which could be used for highly selective and sensitive fluorescence turn-on detection of cyanide in aqueous media. The CX showed selective fluorescence recognition for CN^?, the miscellaneous competitive anions (F^?, Cl^?, Br^?, I^?, AcO^?, H₂PO₄^?, HSO₄^?, ClO₄^?, S^2?, PO₄^3?, CO₃^2? and SCN^?) did not lead to any significant interference. The detection limit of the sensor towards CN^? is 1.15 × 10^?7 mol?L^?1. The sensor has been successfully applied to estimate the cyanide ion in seeds of cherries. Test strips based on CX were fabricated, which could be used as a convenient and efficient CN^? test kit to detect CN^? in aqueous solution for “in-the-field” measurement.

Full text of DOI:10.1002/cjoc.201600811

FULL PAPER
DOI: 10.1002/cjoc.201600811
A Turn-On Fluorescence Chemosensor for Cyanide in Aqueous
Media Based on a Nucleophilic Addition Reaction
Jie Chen, Wenting Li, Qiao Li, Qi Lin, Hong Yao, Youming Zhang, and Taibao Wei*
Key Laboratory of Eco-Environment-Related Polymer Materials, Ministry of Education of China; Key Laboratory
of Polymer Materials of Gansu Province; College of Chemistry and Chemical Engineering, Northwest Normal
University, Lanzhou, Gansu 730070, China

We synthesized a new cyanide (CN ) chemosensor CX based on a nucleophilic addition reaction prompted by
cyanide ion, which could be used for highly selective and sensitive fluorescence turn-on detection of cyanide in

aqueous media. The CX showed selective fluorescence recognition for CN , the miscellaneous competitive anions





－
4
－
4
－
4
2
3－
2－

(
F , Cl , Br , I , AcO , H
2
PO
, HSO
, ClO
, S , PO
4
, CO
3
and SCN ) did not lead to any significant
−
7
－1
interference. The detection limit of the sensor towards CN is 1.15×10 mol•L . The sensor has been successfully
applied to estimate the cyanide ion in seeds of cherries. Test strips based on CX were fabricated, which could be
used as a convenient and efficient CN test kit to detect CN in aqueous solution for ‘‘in-the-field’’ measurement.
−
−
Keywords cyanide, fluorescent, chemosensor, test kits, seeds of cherries
Introduction
In view of this requirement and as a part of our re-
[
33-38]
search interest in ion recognition,
we attempt to
The selective sensing of important anions is highly
significant because anions are widely distributed and
play important roles in both environmental and life sci-
develop an efficient optical chemosensor which can

sense CN with specific selectivity and high sensitivity.
[
1-7]
Herein, we report a chemosensor CX based on a nucle-
ophilic addition reaction prompted by cyanide ion,
which could be used for highly selective and sensitive
fluorescence turn-on detection of cyanide in aqueous
media (Scheme 1).
ences.
Many efforts have been made to design



－
chemosensors for anions such as F , CN , Cl , H PO ,
2
4
－

[8-19]
SO , AcO , etc.
However, most of the synthetic
4
receptors operate in nonprotonic organic solvents while
few in aqueous solution, and they often require convo-
luted and time-consuming syntheses.
cause it is particularly difficult to develop anion recog-
nition systems that form hydrogen bonded complexes in
aqueous solvent, for the obvious reason that the water
competes strongly for the hydrogen bonding sites.
Cyanide is one among the toxic anions, cyanide ions
could be absorbed through the lungs, skin, and gastro-
intestinal tract leading to vomiting, convulsions, loss of
[
20-24]
This is be-
Scheme 1 Synthesis of sensor molecule CX
O
O
O
O
NH2
OH
Cl
O
O
[
25]
consciousness, and eventually death.
Despite their
1
2
toxicity, their outstanding applications in various indus-
trial processes including electroplating, metallurgy, heap
leaching of gold ore, polymer synthesis, steel manufac-
turing and as raw materials for synthetic fibers, resins
and herbicides are inevitable, which raise the risk of
accidental or intentional release of cyanide ions into the
O
N
H
O
O
CX
[26]
environment as a toxic contaminant.
Therefore, a
large number of good sensors for cyanide have been
Experimental
[27-29]
invented.
Sensitive, selective, simple, low-cost, and

General information and materials
Fresh double-distilled water was used throughout the
easy-to-prepare CN fluorometric chemosensors have
[30-32]
become good choices for various applications.
*
E-mail: weitaibao@126.com; Tel.: 0086-0931-7973191
Received November 21, 2016; accepted December 25, 2016; published online XXXX, 2017.
Supporting information for this article is available on the WWW under http://dx.doi.org/10.1002/cjoc.201600811 or from the author.
Chin. J. Chem. 2017, XX, 1—5
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
1

Chen et al.
FULL PAPER
1
experiments, all other reagents and solvents for synthe-
sis were commercially available at analytical grade and
were used without further purification. All the anions
were added in the form of tetrabutylammonium (TBA),
which were purchased from Sigma-Aldrich Chemicals,
For H NMR titrations, the solution of CX was pre-
pared in DMSO-d and the appropriate concentrated
solution of the guest was prepared in D O. Aliquots of
6
2
the two solutions were mixed directly in NMR tubes.
1
and stored in a vacuum desiccator. H NMR spectra were
Results and Discussion
recorded on a Mercury-400BB spectrometer at 400
MHz. Chemical shifts are reported downfield from tet-
ramethylsilane (TMS, δ scale with solvent resonances as
internal standards). Electrospray ionization mass spectra
The sensing abilities of CX towards various anions






－
－
－
(
CN , F , Cl , Br , I , AcO , H PO , HSO , ClO ,
2 4 4 4

2
3－
2－
SCN , S , PO , and CO3 ) were investigated by
4
fluorescence spectroscopy. We carried out experiments
(ESI-MS) were measured on an Agilent 1100 LC-MSD-
1
2
in the DMSO/H O (8∶2, V/V, containing 0.01 mol•L
Trap-VL system. UV-vis spectra were recorded on a
Shimadzu UV-2550 spectrometer. Photoluminescence
spectra were performed on a Shimadzu RF-5301 fluo-
rescence spectrophotometer. Melting points were meas-
ured on an X-4 digital melting point apparatus (uncor-
rected). Infrared spectra were performed on a Digilab
FTS-3000 FT-IR spectrophotometer.
HEPES, pH 7.20). Free sensor CX exhibited an emis-
sion maximum at 398 nm upon excitation at 335 nm.
After addition of the DMSO solution of these different
3
1
anions (1×10 mol•L ) to the DMSO/H
2
O (8∶2, V/V,
1
containing 0.01 mol•L HEPES, pH 7.20) solution of
sensor CX (2×10 mol•L ), respectively, a significant
fluorescence enhancement was only seen in the case of
CN and none of other anions induced any significant

5
1
−
Synthesis of sensor molecule CX
changes in the fluorescent spectrum of the sensor (Fig-
ure 1). Figure S1 demonstrated the absorption spectral
Coumarin-3-carboxylic acid (3 mmol) and bis(tri-
chlormethyl) carbonate (BTC, 1.5 mmol) were added
into dry dichloromethane (15 mL). Then the reaction
mixture was stirred at 40 ℃ for 3 h under reflux. In
this process, the coumarin-3-carboxylic acid has been
converted to the coumarin-3-carbonyl chloride. The
compound 2 (1 mmol), β-naphthylamine (1.2 mmol)
and catalytic amount of acetic acid (AcOH) and tri-
ethylamine (20 mmL 2.0 g) were combined in hot abso-
lute ethanol and tetrahydrofuran (25 mL). The solution
was stirred under reflux for 4 h. After cooling to room
temperature, the yellow precipitate was filtered, washed
three times with hot absolute ethanol, then recrystallized
3－
2－
and CO3
changes of CX upon the addition of PO4
.
2
with EtOH/H O to give a yellow powder product CX in
1
8
1
8
7
1
1
1
6
5% yield (m.p.＞300 ℃). H NMR (DMSO-d ) δ:
0.88 (s, 1H, NH), 8.97 (s, 1H, ArH), 8.43 (s, 1H, ArH),
.05 (d, J＝7.2 Hz, 1H, ArH), 8.00－7.64 (m, 5H, ArH),
1
3
.64－7.22 (m, 4H, ArH); C NMR (DMSO-d
6
) δ:
Figure 1 Fluorescence emission data for the sensor of CX (2×

5
1
60.94 (s), 160.47 (s), 154.36 (s), 147.87 (s), 135.98 (s),
34.79 (s), 133.80 (s), 130.74 (d), 129.19 (s), 127.96 (d),
27.08 (s), 125.77 (s), 125.55 (s), 120.72 (s), 120.35 (m),
10 mol•L ) with various anions as the tetrabutylammonium
salts, respectively, in the DMSO/H O (8∶2, V/V, containing 0.01
mol•L HEPES, pH 7.20) solution (excitation wavelength＝335
2

1

5
1
1
18.96 (s), 116.60 (s); IR (KBr) v: 3437 (N－H), 1706
nm). Inset: photograph of CX (2×10 mol•L ) upon addition of
1

(C＝O) cm . HR-MS calcd for C20
H13NO
3
: 315.09,
50 equiv. of CN , which was taken under a UV-lamp (365 nm).
＋
found [C20
General procedure for spectroscopy
All the fluorescence spectroscopy was carried out in
3
H13NO ＋H] : 316.09.
To further explore the utility of sensor CX as an
ion-selective chemosensor for CN , competitive exper-
iments were carried out in the presence of 50 equiv. of
−
1




the DMSO/H
-(2-hydroxyethyl)-1-piperazineethanesulfonic
HEPES), pH 7.20) on a Shimadzu RF-5301 spectrom-
2
O (8∶2, V/V, containing 0.01 mol•L
CN and 50 equiv. of various other anions (F , Cl , Br ,


－
－
－

2
3－
4
acid
I , AcO , H PO , HSO , ClO , SCN , S , PO
and CO ) in DMSO/H O (8∶2, V/V, containing 0.01
3
2
,
2
4
4
4
4
2－
(
1
eter. Any changes in the fluorescence spectra of the
synthesized compound were recorded on addition of
tetrabutylammonium salts while keeping the ligand
mol•L HEPES, pH 7.20) for sensor CX. The other
anions did not show any noticeable changes in the emis-
sion maximum band under the same condition. The plot
of changes in the fluorescence intensity at 398 nm upon
addition of various anions clearly showed excellent se-
concentration constant (2.0×10 mol•L ) in all ex-
5
1


periments. Tetrabutylammonium salt of anions (F , Cl ,
Br , I , AcO , H PO , HSO , ClO , SCN , S ,
PO , CO3 and CN ) were used for the fluores-



－
4
－
4
－
4

2
−
lectivity of sensor CX towards the CN (Figure 2).
2
3－
2－

To get further insight into the sensing behavior of
4

cence experiments.
CX to CN , fluorescence titration experiment was per-
2
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© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Chin. J. Chem. 2017, XX, 1—5

A Turn-On Fluorescence Chemosensor for Cyanide in Aqueous Media
mained quite stable, suggesting that the binding process
might be completed instantly and the chemosensor has
rapid detection ability for cyanide ions.
500
450
400
350
300
250
200
150
100
Figure 2 Fluorescence spectra response of CX (2×105 mol•

1
2
L ) in the presence of various anions (50 equiv.) in DMSO/H O
0
20
40
60
80

1
(
8∶2, V/V, containing 0.01 mol•L HEPES, pH 7.20) in re-
−
Time/s
sponse to CN ( 50 equiv.)
Figure 4 Fluorescence intensity at 398 nm for CX (2×10
5

1
1
formed. With the gradual addition of pure water solution
2
mol•L ) in DMSO/H O (8∶2, V/V, containing 0.01 mol•L

−
3
1
of CN to sensor CX, the emission peak at 398 nm
HEPES, pH 7.20) after addition of CN (1×10 mol•L ).
gradually enhanced intensity, and the fluorescence of
CX essentially reached saturation by 14 equivalents of
To explore the sensing mechanism of sensor CX to

−
1
CN (Figure 3). In other words, the free sensor CX was
CN , the H NMR titration and MS were investigated,
which illustrated the characteristic structural changes

non-emissive, when it encountered CN , it resulted in a

dramatic enhancement of the fluorescence intensity.
Meanwhile, the fluorescence quantum yields increased
from 0.047 to 0.22 (in ESI). On the basis of fluores-
occurring upon interaction with CN . As shown in Fig-
ure 5, before the addition of cyanide anions, the
HNMR chemical shifts of H and H (N－H) appeared
a b
1

cence titration data, the binding constant of CX for CN
at δ 8.97 and 10.88, respectively. With the gradual addi-
5
1

was calculated to be K＝1.25×10 mol•L (in ESI). In
the meantime, the detection limit of the fluorescence
spectra changes calculated on the basis of 3σB/S was
tion of CN , protons H
signal at δ 11.43 of H
peak (H ) at δ 8.97 disappeared, whereas new signals at
b
at CX disappeared and a new
appeared. At the same time, the
b
a
7
1
−
[39]
1
.15×10 mol•L for CN (in ESI).
δ 5.10 evolved. These results implied the nucleophilic

attack of CN was added to coumarin group in CX,
b
simultaneously, the －CN formed H …CN hydrogen
bond (Scheme 2). Further evidence obtained by MS ex-
periments also supports this proposed mechanism. In the
HR-MS spectrum of CX (Figure S5, in ESI), probe CX
400
300
200
100
0
1
4 equiv.
-
+
CN
displays a peak at m/z 316.09 assigned to CX (m/z calcd

0
equiv.
3
15.09). However, when 1 equivalent of CN was added
to the solution of CX, a peak at m/z 365.12 ([CX＋NaCN
＋
＋
H] ) (Figure S6, in ESI) appears along with the dis-
appearance of the peak at m/z 316.09. It is proved to be

the ratio of 1∶1 between CX and CN .
Scheme 2 Proposed sensing mechanism of sensor CX for the
400
600
−
detection of CN
Wavelength/nm
Figure 3 Fluorescence spectra of CX (2×10 mol•L ) in
5
1

1
DMSO/H O solution (8 ∶2, V/V, containing 0.01 mol•L
2

HEPES, pH＝7.20) upon addition of increasing CN .
As known, chemosensors always have a problem of
long response time. In our case, the binding process of

CN to CX was found to be very fast (Figure 4). After

3
1
adding CN (1×10 mol•L ), the fluorescence emis-
sion intensity of CX was increased at 398 nm and
reached the plateau region in less than 10 s, and re-
To investigate the practical application of sensor CX,
Chin. J. Chem. 2017, XX, 1—5
© 2017 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
www.cjc.wiley-vch.de
3

Chen et al.
FULL PAPER
Table 1 Determination of cyanide content in CNCS samples (n＝3)

－1

－1
－1
Sample
Determind CN /(µmol•L
)
Adding CN /(µmol•L
)
Found/(µmol•L
)
Recovery/%
RSD/% (n＝3)
1
2
3
4
2.27
2.27
2.27
2.27
0.5
1.0
1.5
2.0
2.75
3.29
3.88
4.25
96%
102
107
99
0.6
1.0
0.9
1.2
recovery of 101% with Relative Standard Deviation
RSD) of 0.92% for CNCS samples (Table 1). The ex-
(
perimental results indicate that the sensor possesses ex-
cellent applicability for real sample analysis.
Conclusions
In summary, we have presented a facile, low-cost
and efficient example of a highly selective chemosensor
−
for CN . The sensor gives an immediate response to the
cyanide ion by fluorescence turn-on response. The de-
tection of cyanide ion in solution using CX was found
to be free of interference from any other anions. More-
over, the sensor demonstrates that the detection limit on

1
1
fluorescence response of it to CN is down to 1.15×
Figure 5 Partial H NMR spectra of CX (0.01 mol•L ) in
7
－1
−
10 mol•L , which is far lower than the maximum
DMSO upon addition of CN .
6
1
level of 2.7×10 mol•L for cyanide in drinking water
according to WHO guidelines. In addition, test strips
based on CX were fabricated, which also exhibited a
good selectivity to CN as in solution. Notably, the
chemosensor was successfully applied to the detection
of cyanide in cherry nut. So this recognition behaviour
we prepared test strips by immersing filter papers into
the DMSO/H O (8∶2, V/V, containing 0.01 mol•L
2
HEPES, pH 7.20) of sensor CX (1×10 mol•L ), and
1

3
1
then drying them in air. As shown in Figure 6, when the
test strips coated with CX (1×10 mol•L ) were im-
3
1


mersed into the pure water solutions of CN , the obvi-
makes CX a potential probe to detect CN in our lives
ous fluorescence turn-on response can also be observed
upon irradiation at 365 nm by a UV lamp. The devel-
opment of such a ‘dip-stick’ approach is extremely at-
tractive for ‘in-the-field’ measurements that do not re-
quire any additional equipment. Therefore, the test strips
of CX have excellent application value in the detection
and environment.
Acknowledgement
This work was supported by the National Natural
Science Foundation of China (Nos. 21161018,

2
1262032, 21574104), the Program for Chang Jiang
of CN .
Scholars and Innovative Research Team in University of
Ministry of Education of China (No. IRT1177).
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