Highly selective and sensitive chemosensor based on 2,3-diaminophenazine hydrochloride for the detection of cyanide in pure water and its application in plant seed samples

Article abstract of DOI:10.1039/c8nj02316f

In this study, we prepared an efficient chemosensor based on 2,3-diaminophenazine hydrochloride, and it exhibited good dissolvability in water; more importantly, it could act as an efficient chemodosimeter for the selective detection of CN^- in pure water. Upon reacting with CN^-, 2,3-diaminophenazine hydrochloride (Q1) displayed a remarkable visible and fluorescence response simultaneously with significant changes in both absorption and fluorescence spectra. Furthermore, the absorption and fluorescence detection limits of CN^- were 1.95 × 10^-7 M and 1.13 × 10^-9 M, respectively. For practical applications, test strips based on this chemosensor could serve as convenient CN^- detection tools. The chemosensor was also successfully applied to the detection of CN^- in plant seeds and several natural water samples.

Full text of DOI:10.1039/c8nj02316f

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PAPER
Jason B. Benedict et al.
The role of atropisomers on the photo-reactivity and fatigue of
diarylethene-based metal–organic frameworks
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High selectivity and sensitivity chemosensor based on 2, 3-
Diaminophenazine hydrochloride for detection of cyanide in pure
water and its application in plant seeds sample
Received 00th January 20xx,
Accepted 00th January 20xx
Bi-Rong Yong, Tai-Bao Wei*, Wen-Juan Qu*, Qi Lin*, You-Ming Zhang, Hong Yao
DOI: 10.1039/x0xx00000x
In this work, we prepared an efficient chemosensor base on hydrochloride of 2,3-diaminophenazine which
has good dissolvability in water, and more importantly, it can be act as an efficient chemodosimeter
approach for the selective detection of CN− in pure water. Upon treating with CN−, 2,3-diaminophenazine
hydrochloride (Q1) displayed a remarkable naked-eye and fluorescent response, simultaneously with
significant changes in absorption spectra and fluorescent spectra. Furthermore, the absorption and
fluorescent detection limit of CN− was 1.95×10-7 M and 1.13×10-9 M, respectively. As practical applications,
the test strips based on the chemosensor could serve as convenient CN− detected tools. And it also
successfully applied to the detection of CN− in plant seeds and several natural water samples.
www.rsc.org/
most of these methods are costly and time-consuming, the
CN− sensors often employ sophisticated structures and require
complicated synthetic steps and high temperature, moreover,
Introduction
Prior to this, a large number of studies on the properties of
phenazine and its derivatives have been reported[1]. However,
there is no reports of the 2,3-diaminophenazine hydrochloride.
As we all know, 2,3-diaminophenazine has a poor solubility
which limits its scope of application. However, we have found
that after acidified with hydrochloric acid it has a good
dissolvability in pure water. More importantly, it can be used
to act efficiently in a chemodosimeter approach for the
selective detection of CN− in pure water.
they have a poor solubility in pure water or the tests are
carried out in organic solvents[9] (Scheme 1), thus limiting their
applications. Hence, it is worthy of serious consideration to
find a new method to rapidly, simple and highly selective and
sensitive detection of CN− in pure water. Different from the
previous reports, here, it is concluded that the probe Q1 must
be a promising its selectivity, ease-of-use, rapid response
(response time about 3 s), and the low, naked-eye discernible
CN−, and it can be used to act efficiently in a chemodosimeter
approach for the selective detection of CN− in pure water.
What is more, to our knowledge, there is no published
information that 2,3-diaminophenazine hydrochloride is highly
selective and sensitive detection of CN− in pure water.
Cyanides received wide attention because of their
extremely toxic effect towards humans and they were
regarded as environmental inorganic pollutants[2]. A small
amount of cyanide is present in certain seed, e.g., those of an
apple, mango, peach and bitter almonds[3].There are also
found in cigarette smoke, in vehicle exhaust and formed by the
incomplete combustion of all nitrogen-containing substances[4].
Due to the wide range of application, the large amount of CN−
pollutants was produced by mining and jewelry industries into
the environment[5], the World Health Organization (WHO)
recommended a tolerable limit of CN− at 1.9 µM[6]. Based on
these, it is very important to find a highly efficient and quick
identification of CN− in pure water[7]. Although previously have
We found the progress of recognition could be hydrogen
bonding in the labile of primary amine salt on Q1 and CN−, and
they formed through Q1 and CN− 1: 2 ratio. When exposed Q1
to the CN− solution of low concentration, there was a
significant color change from yellow-orange to bright yellow in
visible light and accompanied with a strong and broad blue
shift. However, without any signal changes after the addition
−
−
−
of F−, Cl−, Br−, I−, AcO−, H2PO4 , HSO4 , ClO4 , SCN− and S2-, the
absorption spectra detection limit of Q1 for CN− was 1.95×10-7
M, and the fluorescent color change from dark red to bright
yellow, the fluorescence spectra detection limit was 1.13×10-9
M and other common anions had almost no influence on the
probing behavior of CN−. Meanwhile, test strips based on
sensor Q1 were fabricated and it was also successfully applied
to the detection of CN− in bitter almonds and wild peach
kernel. Besides, it has been tested in river water and lake
water.
a large number of document reports are used to detect CN− [8]
,
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. E-mail: weitaibao@126.com,
quwenjuanlz@163.com; linqi2004@126.com
.
† Electronic supplementary information (ESI) available: Complete experimental
procedures and some of the spectroscopic techniques.
See DOI: 10.1039/x0xx00000x
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Scheme 1. Tactics for the sensing of CN−.
Fig. 2 Absorbance response of Q1 (2.0 × 10−5 M) in the presence
of 5 equiv. various anions containing 5 equiv. of CN- in fresh
distilled water at room temperature.
Notably, this 2,3-diaminophenazine hydrochloride can be
used as a green, non-toxic, pollution-free and high selectivity,
sensitivity chemosensor to detection of CN− in pure water on
the basis of these observations and mechanistic supported
analyses.
Synthesis and characterization of chemosensor
Q1
Results and discussion
In order to investigate the CN− recognition abilities and progress
of Q1 in pure water, we carried out a series of recognition
experiments. The recognition profiles of Q1 (2.0 × 10−5 M) toward
2,3-diaminophenazine was prepared according to the literature
procedure[10], chemosensor 2,3-diaminophenazine hydrochloride
(Q1) were synthesized according to the Scheme S1†. All complexes
were unambiguously characterized by 1H NMR spectroscopy, 13C
NMR spectroscopy, ESI mass spectrometry, FT-IR (Experimental
section for further details can be seen in Supporting Information).
various anions, including F−, Cl−, Br−, I−, AcO−, H2PO4 , HSO4−, ClO4
−
−
and sodium salt (1.0 × 10−3 M) of anions (CN−, SCN− and S2-) were
primarily investigated using UV–vis spectroscopy in fresh distilled
water. As shown in Fig. 1, in the absorbance spectrum, the
maximum emission of Q1 appeared at 448 nm. When 5 equivalents
of CN− was added to the solution of Q1, there was a significant color
change from yellow-orange to bright yellow and accompanied with
a strong and broad blue shift, which was visible to the naked eyes in
1
Q1 as dark brown solid and has a good solubility in pure water, H
NMR (D2O, 600 MHz) δ: 7.61 (s, 4H); 7.51 (s, 2H); 6.51 (s, 6H). 13C
NMR (DMSO-d6, 150 MHz) δ/ppm 149.53, 132.57, 129.11, 127.75,
2+
123.02, 96.88. ESI-MS calcd for C12H12N4 212.1051, found
212.1010.
Fig. 1 Absorbance spectra of target compound Q1 (2.0 × 10−5 M)
in fresh distilled water presence of CN− and other anions (5
equiv.). Inset: photograph showing the change in color of the
solution of Q1 in fresh distilled water after addition of CN− and
other anions in visible light.
Fig. 3 Fluorescence spectra of target compound Q1 (2.0 × 10−5
M) in fresh distilled water presence of CN− and other anions (5
equiv.). Inset: photograph showing the change in color of the
solution of Q1 in fresh distilled water after addition of CN− and
other anions at UV lamp (excitation wavelength = 410 nm).
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Fig. 6 Fluorescence spectra of Q1 (2.0 × 10−5 M) in various
concentrations of CN− are acquired in fresh distilled water.
Fig. 4 Fluorescence response of Q1 (2.0 × 10−5 M) in the
presence of 5 equiv. various anions containing 5 equiv. of CN- in
fresh distilled water at room temperature.
Inset:
a plot of fluorescent intensity depending on the
concentration of CN− in the range from 0 to 1.08 equivalents.
Each measurement was done at room temperature of mixing
for Q1 and CN− in fresh distilled water (excitation wavelength
= 410 nm).
fresh distilled water. Furthermore, the selectivity of Q1 for CN− over
other anions was examined. The results revealed that all potentially
−
competitive anions (F−, Cl−, Br−, I−, AcO−, H2PO4−, HSO4 , ClO4−, SCN− intensity changes were not monitored obviously by other anions
and S2-) exerted no or little influence on the UV–vis detection of CN− but were just comparable to Q1 itself. Meanwhile, the fluorescence
in fresh distilled water (Fig. 2). To evaluate the selectivity of Q1, we color change from dark red to bright yellow and it could be
measured the fluorescence intensive of Q1 in the presence of distinguished by a UV lamp at 365 nm as shown in Fig. 3.
−
−
various anions (F−, Cl−, Br−, I−, AcO−, H2PO4 , HSO4 , ClO4−, CN−, and Competitive assay also showed consistent evidence that Q1 only
SCN−). As shown in Figure 3, in the fluorescence spectrum, the was transformed by CN−. The fluorescence intensity of Q1 and other
maximum emission of Q1 appeared at 562 nm in fresh distilled anions was restored as much as that of Q1-CN by addition of CN− to
water when λex = 410 nm. On the addition of 5 equivalents of CN−, the mixture of Q1 and other anions (Fig. 4).
the fluorescence intensity of sensor Q1 (20 μM) increased rapidly.
To further investigate the interaction between probe Q1 and CN−,
The fluorescence maximum intensity of Q1 was dramatically change the variation in the UV–vis absorption spectral of probe Q1 (20 μM)
almost 26 times after the addition of CN−, whereas the fluorescence in fresh distilled water was recorded during the titrations with
different concentrations of CN− from 0 to 1.96 equivalents. As
shown in Fig. 5, an isosbestic point at 410 nm was clearly observed
with increasing concentrations of CN−. At the same time,
fluorescence emission spectral variation of probe Q1 (20 μM) in
fresh distilled water was monitored during titrations with different
concentrations of CN− from 0 to 1.08 equivalents (Fig. 6). With an
Fig. 5 Absorption spectrum of Q1 (2.0 × 10−5 M) in various
concentrations of CN− are acquired in fresh distilled water.
Inset: a plot of absorbance intensity (emission at 448 nm)
depending on the concentration of cyanide in the range from 0
Fig. 7 Titration curves of 1H NMR spectra of Q1 (0.01 M) in D2O
upon addition of CN− (1 M, D2O).
to 1.96 equivalents. Each measurement was done at room
temperature of mixing for Q1 and CN− in fresh distilled water.
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Fig. 10 Photographs of test strips: only Q1 (2×10−4 M), Q1 and
other anions, Q1-CN, Q1-CN and other anions (from left to
right).
Fig. 8 Chemical structures of Q1 and Q1-CN and the reaction
mechanism in this system.
increasing amount of CN−, fluorescence intensity of sensor Q1 (λem
= 562 nm) gradually increased. A plot of absorbance intensity
depending on the concentration of CN− in the range from 0 to 1.96
equivalents was drawn. Similarly, a plot of fluorescent intensity
depending on the concentration of CN− in the range from 0 to 1.08
equivalents (excitation wavelength = 410 nm) was drawn. Each
measurement was done at room temperature of mixing for Q1 and
CN− fresh distilled water. Furthermore, to determine the detection
limit of Q1, the UV–vis absorption spectral and the fluorescent
spectrums of blank tests were measured 20 times and the standard
deviation of the blank measurements was determined. The linear
fitting was performed according to the titrations curves, and the
mean intensity was calculated to determine the slope.
Fig. 11 Photographs showing: (a) Q1+Bitter almonds, only Q1
(2×10−4 M), Q1+Wild peach kernel in visible light (from left to
right). (b) Only bitter almonds filtrate, only wild peach kernel
filtrate (from left to right).
was 1.13×10-9 M (Fig. S7). This data indicate that Q1 can detect CN−
at very low concentrations in the environment.
To gain better insight into the sensing mechanism of
chemosensor Q1 to CN−, the 1H NMR titration, IR spectrum and ESI-
MS were performed. The recognition mechanism was investigated
by 1H NMR titration of the probe Q1 with CN−. 1H NMR titration
displayed the chemical shift changes of Q1 upon the addition of CN−,
as shown in Fig. 7, sensor Q1 showed peak Ha at δ7.61 ppm, Hb and
Hd at δ7.57 ppm and Hc at δ6.50 ppm in D2O, after the titration we
found that with the addition CN− (concentration from 0 equivalent
to 1.0 equivalent), Ha, Hb, Hc and Hd proton exhibited a downfield
shift on different levels. However, the addition of more CN− led to
the absorbance decreased monotonously which suggest the
decrease in the electron density in the benzene ring and primary
amine salt via hydrogen bonds. Through UV-vis absorbance titration
experiments, we can infer that this process through hydrogen
bonds takes at least two steps. Upon addition of increasing
amounts of CN− to the solution of Q1, a decrease in the absorbance
peak with a hypochromatic shift of Q1 was observed. In this step,
we consider that only one CN− forms a hydrogen bond with the host,
resulting in a blue shift of the absorption peak. After that, as the
concentration of CN− increases, the host bound two molecules of
CN− by hydrogen bonds. At this point, the system becomes stable
and the absorption peak no longer changes (Fig. 8).
The detection limit was calculated using the following equation:
Detectionlimit = 3δ/S (δ is the standard deviation of the absorbance
and emission intensity of Q1 in the presence of CN− and S is the
slope times ten to the sixth between the absorbance/emission
intensity and concentration). Obtained by calculation, the
absorption spectra detection limit of the chemosensor for CN− was
1.95×10-7 M (Fig. S6) and the fluorescence spectra detection limit
Further evidence for the formation of the desired complex was
obtained by ESI-MS, revealing a peak of Q1 at m/z 212.1010 (Fig. S4
in SI), corresponding to [Q1-CN+H]+ revealed a peak at m/z
265.1922, (Fig. S5 in SI), indicating a 1:2 stoichiometry between Q1
and CN−.
Meanwhile, in order to further illustrate the problem, we did the
infrared spectroscopy experiment. In the IR spectrum of Q1, a
stretching vibration absorption double peaks of primary amine salt
Fig. 9 FT-IR spectra of the compound Q1 and Q1-CN complex
powdered in KBr disks.
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Fig. 12 Fluorescence spectra of target compound Q1 (2.0 ×
10−4 M) in the presence of bitter almonds and wild peach
kernel in fresh distilled water on excitation at 410 nm. Inset:
photograph showing the change in color of the solution of Q1
in fresh distilled water after addition of bitter almonds and
wild peach kernel under irradiation at 365 nm by UV lamp
(from left to right).
Fig. 14 Photographs showing: the sensing performances of Q1
and test strips in lake water.
In order to further investigate the practical utilities of probe Q1
in our lives, we prepared bitter almonds and wild peach kernel to
implement this experiment. One gram of dry seed was crushed and
pulverized and the obtained mixture must be vigorously stirred for
15 min. Then the mixture was filtered to obtain the cyanide-
(–NH3+) appeared in 2660 cm−1, and a broad peak appeared in 3032 containing solution. Next, the bitter almond (1 g) was first mashed
cm−1. However, compared with Q1, the Q1-CN absorptions shifted until the extract became turbid. The mixture was filtered and the
showed two new peaks at 3302 and 3187 cm-1, respectively (Fig. 9), filtrate was eluted to obtain the cyanide-containing solution (B).
which indicates primary amine salt reacted with CN− by hydrogen The wild peach kernel in cyanide-containing solution (P) obtained in
bonds when 2.0 equivalents of CN− was added.
the same way. We diluted the B and P with fresh distilled water,
To investigate the practical application of chemosensor Q1, test which ensured this experiment in neutral water, upon the addition
strips were prepared and utilized to sense CN−. As shown in Fig. 10, of the two different CN− solutions to Q1 (2.0 × 10−4 M), the
we prepared test strips by immersing filter papers into pure water fluorescence intensity of sensor Q1 increased rapidly. The color
of Q1 (2.0 × 10−4 M) and then drying in air. The test strips containing change from red-orange to bright yellow could be distinguished by
Q1 were utilized to sense CN− and other anions. When CN− and the naked eyes under natural light (Fig. 11), and the color change
other ions were added on the test kit, respectively, the remarkable from dark red to bright yellow could be distinguished at 365 nm by
colour change was observed only with the CN− solution under UV lamp (Fig. 12). Finally, in order to expand the scope of
natural light and UV lamp at 365 nm. And potentially competitive application of this chemical sensor, we have increased the
ions exerted no influence on the detection of CN− by the test strips. experiment of detecting CN− in natural water by Q1, and we can
Therefore, test strips could conveniently detect CN− in pure water.
also detect CN− in river water and lake water, which also can obtain
good results (Fig. 13 and Fig. 14).
Conclusions
In conclusion, we have found that hydrochloride based on 2,3-
diaminophenazine has a good dissolvability in water and it can be
used to act efficiently in a chemodosimeter approach for the
selective detection of CN− via hydrogen bonding in pure water.
Furthermore, an observable color change of dilute solutions of Q1
under the visible light and fluorescent light when exposed to low
concentrations of CN−. In addition, test strips based on sensor Q1
were fabricated and it was also successfully applied to the detection
of CN− in bitter almonds and wild peach kernel. Meanwhile, in order
to expand the application field, we also detected CN− in a more
complex natural water system. The results show that it can detect
CN− in more complex water systems. Thus, it will be regarded as a
simple and highly efficient chemosensor for detecting CN− and the
chemosensor which can be recognized as an ideal, green probe of
CN− in pure water.
Fig. 13 Photographs showing: the sensing performances of Q1
and test strips in river water.
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This work was supported by the National Natural Science
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New Journal of Chemistry
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DOI: 10.1039/C8NJ02316F
Graphical Abstract
High selectivity and sensitivity chemosensor based on 2,3-Diaminophenazine
hydrochloride for detection of cyanide in pure water and its application in plant
seeds sample
BiꢀRong Yong, TaiꢀBao Wei*, WenꢀJuan Qu*, , Qi Lin*, YouꢀMing Zhang, Hong Yao
In this work, we have found that hydrochloride based on 2, 3ꢀdiaminophenazine has a
good dissolvability in pure water, and more importantly, it can be used to act
efficiently in a chemodosimeter approach for the selective detection of cyanide in
pure water. Upon treatment with cyanide, 2, 3ꢀdiaminophenazine hydrochloride (Q1)
displayed a remarkable nakedꢀeye and fluorescent response. It can detection of
cyanide (CN−) rapidly, simply and has a highly selective and sensitive ability in pure
water. And it also successfully applied to the detection of cyanide in bitter almonds
and wild peach kernel.