A simple chemosensor for the dual-channel detection of cyanide in water with high selectivity and sensitivity

Article abstract of DOI:10.1039/c6ra01758d

We have synthesized a simple chemosensor (HY) of acylhydrazones and used it for colorimetric detection of cyanide anions (CN^-) in DMSO/H₂O (3:7, v/v) mixed solvent. The simple chemosensor displays a specificity response for cyanide over other common anions (F^-, Cl^-, Br^-, I^-, AcO^-, H₂PO₄^-, HSO₄^-, ClO₄^-, and SCN^-) in mixed solution. Upon treatment with cyanide, HY displayed a remarkable naked-eye and fluorogenic response, simultaneously with significant changes in its UV-visible and fluorescence spectra. Furthermore, competitive anions did not show any significant changes both in colour and emission intensity, indicating the high selectivity of the sensor to CN^-. The absorption spectra detection limit of the chemosensor for cyanide was 8.34 × 10^-7 M and the fluorescence spectra detection limit was 2.85 × 10^-8 M. The cyanide test strips based on the chemosensor could serve as a convenient cyanide test kit. Furthermore, the chemosensor was successfully applied to the detection of cyanide in sprouting potatoes.

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PAPER
A simple chemosensor for the dualꢀchannel detection of cyanide in water
with high selectivity and sensitivity
XiaoꢀBin Cheng, Hui Li, Feng Zheng, Qi Lin, Hong Yao, YouꢀMing Zhang and TaiꢀBao Wei*
Received (in XXX, XXX) Xth XXXXXXXXX 20XX, Accepted Xth XXXXXXXXX 20XX
5
DOI: 10.1039/b000000x
We have synthesized a simple chemosensor (HY) of
acylhydrazones and used it for colorimetric detection of
cyanide anions (CN–) in DMSO/H2O (3:7, v/v) mixed
solvent. The simple chemosensor displays specificity
mM), but demand cumbersome sample preparation or costly
analytical instruments.
50
Therefore, it is very necessary to develop sensitive,
selective, cheap, simple, fluorometric and colorimetric
chemosensors for detecting CN–.9 Optical chemosensors for
CN–, in which the change in the absorbance and fluorescence
spectra is found, have been continually investigated due to
10 response for cyanide over other common anions (F−, Cl−,
−
−
−
Br−, I−, AcO−, H2PO4 , HSO4 , ClO4 , and SCN−) in mixed
solution. Upon treatment with cyanide, the HY displayed a
remarkable nakedꢀeye and fluorogenic response, 55 their desirable features including simplicity, high selectivity
simultaneously with the significant changes in its UV–
15 visible and fluorescence spectra. Furthermore, competitive
anions did not showed any significant changes both in
colour and emission intensity, indicating the high
and high sensitivity.10 The design and synthesis of
a
colorimetric and fluorometric chemosensors for CN– has
attracted a great concern because it quantization in CN–
detection
by
easily
absorbance
on
a
UV–vis
selectivity of the sensor to CN–. The absorption spectra 60 spectrophotometer and change in fluorescence on
a
detection limits of the chemosensor for cyanide was 8.34 ×
20 10−7 M and the fluorescence spectra detection limit was
2.85×10–8 M. The cyanide test strips based on the
chemosensor could serve as a convenient cyanide test kits.
fluorescence spectra. The general method for the cyanide
detecting are summary as nucleophilic addition on the
carbonyl units,11 electron–deficient alkenes,12 hydrogen
bonding motifs,13 cyanide complexation,14 and so on. But they
Furthermore, the chemosensor was successfully applied to 65 themselves all have their own drawbacks such as poor
the detection of cyanide in sprouting potatoes.
solubility in aqueous media, long responding time or poor
application in the “naked eye” detecting.15 So due to its
operational simplicity, low cost, and rapid implementation,
chromogenic sensor for the detection of cyanide is highly
70 desirable.
25
Introduction
The orientation on devising and synthesizing novel
chemosensors for detecting anions have already been a
In view of the above, and as a part of our research interest
in ions recognition.16 In this paper, we designed and
synthesized a simple fluorescent and colorimetric sensor HY
for cyanide anion based on a deprotonated mechanism. As its
75 hydroxy (–OH) and amine group (–NH–) are effective targets
for the deprotonated procedure, the cyanide can easily combine
with it, inducing a remarkable change in spectroscopic
properties. With the gradual addition of cyanide, the colour of
the solution changed from colourless to yellow which offers
80 the possibility for us to detect the cyanide by “naked eye”.
And the fluorescence colour of the sensor from yellow to
colourless which similarly can detect cyanide by UV–lamps.
30 potential subject due to the biological, surroundings and
practical applications.1 Among various anions, cyanide (CN–)
is one of the most researched focus anions owing to its high
lethal effect on living body and the surroundings.2
Nevertheless, cyanide anions (CN–) are highly toxic to the
35 organism,3 while CN– is widely used in industrial production,
such as electroplating, gold mining, metallurgy, and the
synthesis of fibers, nylon, and resins industry.4 Strong
complexation of CN– to a heme cell of the cytochrome
paralyzes cellular breathe and causes severely damages to the
40 mid nervous system.5 The cyanide standard in industrial
wastewater is thence stringent requirements: for instance,
Japan’s Ministry of Environment sets its licensing standards at
38.5 mM.6 Precise quantification of CN– in the circumstance
specimen is particularly necessary.7 The majority of analytic
45 methods such as potentiometry, chromatography, and
voltammetry, have been used for CN– detection.8 These
methods successfully detect very low standards of CN– (<0.1
−
−
Other anions such as F−, Cl−, Br−, I−, AcO−, H2PO4 , HSO4 ,
−
ClO4 , and SCN− could not cause any interference.
85
Results and discussion
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30 changes of HY (c=2×10ꢀ5 M) after addition of 50 equivalents of various
anions.
In order to estimate the specific properties for selective
recognition of CN− and colorimetric changes associated with
the chemosensor HY, the chemosensor HY toward CN− was
35 studied by UV–vis absorption spectra titration experiments.
Along with the increasing of concentration of CN−, a
significant increase of the UV–vis absorbance at 420 nm.
Such a red shift led to the solution color changing from
colorless to yellow. On the other hand, a clear isosbestic
40 points are observed at 378 nm (Fig. 3). Similarly, the
fluorescence spectra of the chemosensor HY change
significantly along with the concentration increase of CN−.
The intensity of the fluorescence band centered at 512 nm of
chemosensor HY decreased progressively along with the
45 concentration increase of CN−, and it was quenched almost
completely after the addition of CN− (Fig. 4). In the meantime,
the detection limits of the HY for CN− calculated on the basis
of 3δ/S (Figure S4, S5) were 8.34×10−7 M for absorption
spectra and 2.85×10−8 M for fluorescences spectra change
50 respectively, which are both far lower than the WHO
guideline of CN− in drinking water (less than 1.9×10ꢀ6 M). In
addition, the fluorescence quantum yields weakened from
0.64 to 0.007.
Scheme 1. Structure and synthesis of the chemosensor HY.
The synthetic procedure of chemosensor HY is shown in
1
Scheme 1. The chemosensor HY has been characterized by H
5
NMR, 13C NMR, IR and ESI–MS (Figure S1–S3).To detect the
selectivity of HY towards CN−, we carried out a series of spectral
experiments, where 50 equiv. of various anions (F−, Cl−, Br−, I−,
−
−
−
AcO−, H2PO4 , HSO4 , ClO4 , CN−, and SCN−) were respectively
added to 2.0 × 10−5 M of HY in mixed solution (DMSO/H2O,
10 3:7, v/v). When adding 50 equiv. of CN− to the solution of sensor
HY, the HY responded with dramatic color changes from
colorless to yellow (Fig. 1 inset). As shown in Fig. 1, in the
corresponding UV–vis spectrum, a strong and broad absorption
band from 378 to 460 nm was observed for the chemosensors
15 HY. However, as shown in Fig. 2, a yellow fluorescence with one
emission band centered at 512 nm appeared when the solution of
chemosensors HY was excited at 378 nm. Upon the addition of
CN− solution, the yellow fluorescence emission band decreased
remarkably. A variety of other anions, such as F−, Cl−, Br−, I−,
−
−
−
20 AcO−, H2PO4 , HSO4 , ClO4 , and SCN−, did not cause such a
significant change.
55 Fig. 3. UV–vis spectra of HY (2.0 × 10−5 M) in DMSO/H2O (3:7, v/v)
upon adding an increasing concentration of CN− (0.1 M). Inset: a) Color
change; b) a plot of absorption at 420 nm versus number of equivalents of
CN−.
Figure 1. UV−Vis spectra of HY (c=2×10ꢀ5 M) after addition of 50
equivalents of various anions. Inset: UV−vis color changes of HY
25 (c=2×10ꢀ5 M) after addition of 50 equivalents of various anions (c=1×10ꢀ2
M).
Fig. 2. Fluorescence spectra (λex=378 nm) of HY (c=2×10ꢀ5 M) after
addition of 50 equivalents of various anions. Inset: Fluorescent color
2
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Fig. 4. Fluorescence spectra of HY (2.0 × 10−5 M) in DMSO/H2O (3:7,
v/v) upon adding an increasing concentration of CN− (0.1 M). Inset: a plot
of emission at 512 nm versus number of equivalents of CN−.
different pH values. The results indicated that HY binding with
CN− occurred effectively in the range of pH 5–14.
To further exploit the utility of the chemosensor HY as
anionꢀselective sensor for CN−, competitive experiments were
carried out in the presence of 50 equiv. of CN− and 50 equiv. of
various anions in (DMSO/H2O, 3:7, v/v) solution. As shown in
Fig. 5, it is noticeable that the miscellaneous competitive anions
did not lead to any significant interference. The fluorescence
5
10 selectivity was examined at an excitation wavelength of 378 nm,
as shown in Fig. 6, all the competing anions did not interfere in
the detection of CN−. This result displayed highly selectivity of
the chemosensor HY toward cyanide anion over other analytes
mentioned above.
Fig. 7. Effect of pH on the absorbance spectra (460 nm) of HY+CN−
30 (50 equiv.) from 1 to 14 in DMSO/H2O (3:7, v/v) solution.
15
Fig. 5. UV–vis spectra of sensor HY at 460 nm with addition of 50 equiv.
of CN− in the presence of 50 equiv. of other anions in DMSO/H2O (3:7,
v/v).
Fig. 8. Effect of pH on fluorescence spectra (512 nm) of HY+CN−
(50 equiv.) from 1 to 14 in DMSO/H2O (3:7, v/v) solution.
To gain better insight into the sensing mechanism of
1
35 chemosensor HY to CN–, the H NMR titration, IR spectrum
1
and ESI–MS were carried out. In the H NMR titration spectra
1
(Fig. 9), before the addition of cyanide anions, the H NMR
chemical shifts of the O−Ha, O−Hb and −NHc− protons on HY
were at δ 12.75, 12.23 and 11.29 ppm. With the addition CN–,
40 the hydroxy proton Ha and Hb, −NH− proton Hc completely
disappeared by the deprotonation. Upon the gradual addition
of CN−, all naphthalene ring protons exhibited an upfield shift
on different levels, which suggest the increase in the electron
density in naphthalene ring through charge delocalization in
45 the conjugated system. Meanwhile, we also did the infrared
spectroscopy experiments to prove mechanism. In the IR
spectrum of HY, the stretching vibration absorption peaks of
hydroxyl O–H and HC=N appeared in 3409 cmꢀ1, 1607 cmꢀ1,
respectively. However, when HY met with CN–, the stretching
50 vibration peaks of hydroxy (O–H) and HC=N absorption
miraculously disappeared (Figure S6). This is clear proof of
20 Fig. 6. Fluorescence of sensor HY at 512 nm with addition of 50 equiv. of
CN− in the presence of 50 equiv. of other anions in DMSO/H2O (3:7, v/v).
The pH dependence of the chemosensor in (DMSO/H2O, 3:7,
v/v) solution system was checked using its absorption spectrum at
420 nm (Fig. 7) and fluorescence spectroscopy emission at 512
25 nm (Fig. 8). Cyanide ion was added to the solution of HY at
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the HY encounter CN– occurred deprotonation effect. 25 Fig. 10. Left: color change of test strips upon addition of CN–. Right: the
Moreover, from the ESI–MS data, we can also see an obvious
peak at m/z 422.9846 assignable to [HY–3H++3Na+] (m/z
called = 422) (Figure S7). This similarly supports the
deprotonation phenomena of HY. These common
detection of test strips upon addition of CN– under an UV lamp at 365 nm.
It is worth mentioning that we also investigated the practical
utilities of the sense in our daily life, we selected the sprouting
potatoes to carry out the below experiment. The sprouting potato
5
phenomenon could be explained from the propose sensing 30 (187 g) was first mashed before being soaked in water (400 mL)
mechanism show in Scheme 2.
for 5 days until the extract became muddy. The mixture was
filtered and the filtrate was washed with 60 mmol/L NaOH
solution (150 ml) to get the cyanide−containing solution. As
shown in Figure 10, upon the addition cyanide−containing
35 solution into HY, An obvious colour change from colourless to
yellow this can be directly observed by the naked eye (Fig. 11a).
And with imagine the unanimous yellow fluorescent disappear
under the UV lamp confirming that HY is a promising CN− probe
for practical applications (Fig. 11b).
Fig. 9. 1H NMR spectra of HY (0.1 M, DMSO−d6) and in the
10 presence of varying amounts of CN−.
40
Fig. 11. Fluorescence emission data for the chemosensor HY to detect
cyanide in sprouting potato. Inset: a) color changes observed for HY upon
the addition of cyanide−containing ; b) color changes observed for HY
upon the addition of cyanide−containing under the UV lamp and
45 photograph of sprouting potato.
Scheme 2. The sensing mechanism of the chemosensor HY to CN–.
Motivated by the favourable CN− recognition properties
of chemosensor HY, we prepared test strips by immersing
15 filter papers into the DMSO/H2O (3 : 7) solution of the
chemosensor HY (1×10−3 M) and then dried them in air. The
test strips could conveniently detect CN−, similar to that
commonly used for the pH measurement. Upon the addition of
CN− solutions to the test strips, the test strips shown obvious
20 color change from colorless to yellow, meanwhile, under the
UV−lamp, the yellow fluorescence were disappear that can be
clearly observed (Fig. 10). Therefore, the test strips of HY
have excellent application value in detection CN−.
Conclusions
In summary, we have developed a novel CN− chemosensor,
50 which could detect CN− through UV “turn−on” and fluorescent
quenching with specific selectivity and high sensitivity. The
investigation of the recognition mechanism indicated that the
chemosensor HY recognized CN− by a deprotonated procedure.
It’s worth noting that the competitive anions did not afford any
55 obvious interference response. The absorption spectra detection
limits of the HY for CN− was 8.34 × 10−7 M and the fluorescence
spectra detection limit was 2.85×10–8 M, which is far lower than
the WHO guideline of CN− in drinking water (less than 1.9×10−6
M). Moreover, test strips based on this chemosensor were
60 fabricated, which could serve as practical colorimetric and
fluorescence test kits to detect CN− for simple and fast
measurement and the chemosensor HY is a good way to detect
cyanide aqueous extracts of sprouting potatoes.
This work was supported by the National Natural Science
65 Foundation of China (NSFC) (no. 21574104; 21161018;
21262032), the Natural Science Foundation of Gansu Province
4
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A simple chemosensor for the dual-channel detection of
cyanide in water with high selectivity and sensitivity
Xiao-Bin Cheng, Hui Li, Feng Zheng, Qi Lin, Hong Yao, You-Ming Zhang and Tai-Bao 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，P. R. China
By a deprotonated mechanism, the simple chemosensor HY showed high sensitivity and selectivity for
cyaniade in aqueous media. Moreover, the chemosensor HY is a good cyaniade test kits. It could detect
cyanide in aqueous extracts of sprouting potatoes.