A novel dual-channel chemosensor for CN- based on rhodamine B hydrazide derivatives and its application in bitter almondf

Article abstract of DOI:10.1039/c7ra09174e

In this article, we successfully designed and synthesized a novel chemosensor PW bearing rhodamine B hydrazide and 8-formyl-7-hydroxyl-4-methylcoumarin, which displayed both colorimetric and "turn-on" fluorescence responses for CN^- in DMSO/H₂O (1: 1, v/v, pH = 7.20) solution. The probe could distinguish CN^- via a deprotonation process and the mechanism of intramolecular charge transfer (ICT), which was proved by ¹H NMR titration, ESI-MS and DFT calculations. The detection limit of the sensor PW towards CN^- was 1.592 × 10^-7 M. Moreover, the sensor PW was successfully utilized to detect CN^-in bitter almond. Test strips containing PW were also prepared, which could act as a colorimetric tool to detect CN^- in practical application.

Full text of DOI:10.1039/c7ra09174e

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PAPER
ꢀ
A novel dual-channel chemosensor for CN based
on rhodamine B hydrazide derivatives and its
Cite this: RSC Adv., 2017, 7, 46832
application in bitter almond†
Peng-Xiang Pei, Jing-Han Hu, * Peng-Wei Ni, Chen Long, Jun-Xia Su and You Sun
In this article, we successfully designed and synthesized a novel chemosensor PW bearing rhodamine B
hydrazide and 8-formyl-7-hydroxyl-4-methylcoumarin, which displayed both colorimetric and “turn-on”
ꢀ
fluorescence responses for CN in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20) solution. The probe could
ꢀ
distinguish CN via a deprotonation process and the mechanism of intramolecular charge transfer (ICT),
Received 19th August 2017
Accepted 27th September 2017
1
which was proved by H NMR titration, ESI-MS and DFT calculations. The detection limit of the sensor
ꢀ
ꢀ7
ꢀ
PW towards CN was 1.592 ꢁ 10 M. Moreover, the sensor PW was successfully utilized to detect CN
in bitter almond. Test strips containing PW were also prepared, which could act as a colorimetric tool to
DOI: 10.1039/c7ra09174e
ꢀ
rsc.li/rsc-advances
detect CN in practical application.
due to low cost, simplicity, high selectivity, sensitivity and fast
1
. Introduction
24
response.
Our research group has a longstanding interest in molec-
In recent years, the design and exploration of articial sensors
25–39
for recognizing cations and anions have received immense ular recognition.
Herein, we designed a novel chemosensor
interest due to their important roles in biological, environ- PW based on rhodamine B hydrazide derivatives, which
1–4
ꢀ
ꢀ
mental, and industrial processes. It is well known that CN is showed a dual-channel response for CN in DMSO/H O (1 : 1,
2
29–33
considered as the most hazardous one of various anions, and it v/v, pH ¼ 7.20) solution. To the best of our knowledge,
most
ꢀ
1
is lethal to humans at concentrations of 0.5–3.5 mg kg body of sensors based on rhodamine B derivatives were mainly
5–7
ꢀ
weight. However, trace amounts of CN also affect many utilized on the recognition of metal ions, and were rarely re-
functions such as blood vessels, visual sense, central nervous, ported for the recognition of anions, especially for CN .
ꢀ
8–11
heart and metabolic systems
in the human body. The World Furthermore, we found that sensors based on rhodamine B
Health Organization (WHO) has set the maximum acceptable derivatives usually recognized metal ions by opening rings,
ꢀ
12,13
amount of 1.9 mM for cyanide ion in drinking water.
however, the sensor PW recognized CN by deprotonation
However, cyanide salts are widely utilized in various industries process, and the ring had no any change in PW. In addition,
such as gold extraction, synthetic bers, electroplating, and the reason for the introduction of rhodamine B is owe to its
1
4–16
metallurgy etc.,
which lead to a serious harm to environment good water solubility and strong uorescence, which makes
ꢀ
and human health. Thus, the rational design and synthesis of clearer for recognition of CN in real sample. On account for
efficient sensors to selectively recognize CN is signicantly these advantages, we believe that the sensor PW shows great
ꢀ
important.
In the past few decades, a variety of analytical methods such
as ion chromatography, potentiometric, titrimetric and elec-
promise for its potential applications.
2
. Experimental
17–20
trochemical methods
have been reported for the investiga-
ꢀ
2.1. Reagents and apparatus
tion of CN . However, those methods usually suffer from
a series of shortages like high cost, long response time, All reagents and solvents were obtained from the commercial
sophisticated equipment and so on, which are serious stum- sources without further purication. Double-distilled water was
2
1–23
bling blocks to its practical application.
In contrast, uo- used throughout the experiment. Tetrabutylammonium salt of
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
rometric and colorimetric sensors have gained more attention anions (F , Cl , Br , I , AcO , H PO , ClO4 and HSO4 ) and
2
4
ꢀ
ꢀ
sodium salt of anions (CN and SCN ) were purchased from
Alfa-Aesar Chemical Reagent Co. and stored in vacuum desic-
cators. H NMR and C NMR spectra were respectively recorded
on a Mercury-400BB spectrometer at 400 MHz and 100 MHz,
College of Chemical and Biological Engineering, Lanzhou Jiaotong University,
Lanzhou, gansu, 730070, P. R. China. E-mail: hujinghan62@163.com
1
13
†
Electronic supplementary information (ESI) available. CCDC 1563205. For ESI
and crystallographic data in CIF or other electronic format see DOI:
0.1039/c7ra09174e
and chemical shis were recorded in ppm (DMSO-d
6
as
1
solvent). Melting points were measured on an X-4 digital
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Scheme 1 The synthesis process of PW.
Fig. 1 Single-crystal X-ray structure of sensor PW.
Fig. 3 Fluorescence spectra of PW (20 mM, lex ¼ 320 nm, lem ¼ 512 nm)
with various anions (50 equiv.) in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20). Inset:
color changes observed for PW (20 mM) with various anions (50 equiv.) in
DMSO/H
O (1 : 1, v/v, pH ¼ 7.20) solution under the UV lamp.
2
2.2. Synthesis of 8-formyl-7-hydroxyl-4-methylcoumarin
4-Methylumbelliferone (10 g, 0.057 mol) and methenamine
(
20 g, 0.143 mol) were mixed in acetic acid (75 ml), and reuxed
ꢂ
for 5.5 h at 95 C, then added 150 ml hydrochloric acid
(
HCl/H
2
O, v/v ¼ 84 : 100) and continued to stir for 0.5 h. Cooling
Fig. 2 UV-Vis spectra of PW (20 mM) in the presence of 50 equiv. of
various anions in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20) binary solution at to room temperature, poured the reaction solution to 750 ml
room temperature. Inset: color changes of PW containing various distilled water and used acetic ether (300 ml) to extract, aer-
2
anions in DMSO/H O (1 : 1, v/v, pH ¼ 7.20) solution.
wards, the acetic ether was washed two times with saturated salt
water, and the extract was evaporated to dry, nally, the
extractive was recrystallized with EtOH to obtain yellow granular
ꢂ
compound in 13%, mp: 179–181 C.
melting point apparatus that was uncorrected. Fluorescence
spectra were performed using a Shimadzu RF-5301 uorescence
spectrophotometer. UV-Vis absorption spectra were measured
2
.3. Synthesis of intermediate rhodamine B hydrazide
on a Shimadzu UV-2550 spectrometer. ESI-MS was measured on Intermediate rhodamine B hydrazide was prepared by one step
an Agilent 1100 LC-MSD-Trap-VL system.
condensation reux reaction of rhodamine B (0.96 g, 2 mmol)
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+
and hydrazine hydrate (1 ml, 0.02 mol) in methanol (30 ml), the
C
39
H
38
N
4
O
6
: [M + H ] ¼ 642, found: 643.2830. The structure of
ꢂ
reaction was stirred for 3 h at 65 C, aer cooling to room sensor PW was further conrmed by single-crystal X-ray
temperature, adjusting pH to 8–9, which emerged lots of pale diffraction (Fig. 1).
pink precipitate, then ltrated and washed three times with
distilled water to obtain light pink compound in 81% yield, mp:
3
. Results and discussion
ꢂ
215–217 C.
The anion-sensing abilities of PW were investigated by UV-Vis
2
spectroscopy and uorescence spectroscopy in DMSO/H O
2.4. Synthesis of PW
Rhodamine B hydrazide (0.46 g, 1 mmol) and 8-formyl-7-
hydroxyl-4-methylcoumarin (0.25 g, 1.2 mol) were reuxed for
ꢂ
6
h in DMF (20 ml) at 85 C, aer cooling to room temperature,
the precipitate was ltrated and recrystallized with DMF-H
2
O to
get light brown compound in 62% yield. As shown in Scheme 1
ꢂ
1
mp > 300 C. H NMR (DMSO-d , 400 MHz, ppm) d: 11.74
6
(
s, 1H), 9.49 (s, 1H), 7.97 (d, J ¼ 8.38 Hz, 2H), 7.66 (dd, J ¼
7
6
6
6
1
1
1
6
.60 Hz, 2H), 7.53 (d, J ¼ 8.38 Hz, 1H), 7.17 (d, J ¼ 7.40 Hz, 1H),
.75 (d, J ¼ 8.87 Hz, 1H), 6.46 (d, J ¼ 8.76 Hz, 3H), 6.37 (m, 2H),
.16 (s, 1H), 3.30 (d, J ¼ 7.70 Hz, 8H) 2.29 (s, 3H), 1.07 (d, J ¼
1
3
6
.86 Hz, 12H). C NMR (DMSO-d , 100 MHz, ppm) d: 164.05,
62.69, 161.06, 159.03, 153.67, 152.77, 151.38, 153.25, 149.12,
45.18, 134.83, 129.52, 128.73, 128.61, 128.25, 124.47, 123.66,
ꢀ
13.68, 112.08, 111.20, 108.76, 105.80, 104.42, 103.57, 97.81,
Fig. 6 Fluorescence detection limit of PW (20 mM) towards CN in
+
6.12, 44.10, 36.19, 31.19, 18.58, 12.76. m/z (ES ) calcd for DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20) solution.
ꢀ
Fig. 4 (a) UV-Vis spectra changes for PW (20 mM) containing various anions in presence of CN in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20) solution. (b)
ꢀ
Fluorescence spectra of PW–CN with various interference anions in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20) solution.
ꢀ
ꢀ
Fig. 5 (a) Absorption spectra titration of sensor PW (20 mM) after addition of different concentration of CN (0–23 equiv.) in DMSO/H
2
O
O
(
(
1 : 1, v/v, pH ¼ 7.20) solution (b) fluorescence spectra of PW in the presence of different concentration of CN (0–37.5 equiv.) in DMSO/H
2
1 : 1, v/v, pH ¼ 7.20) solution.
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ꢀ
ꢀ
(
1 : 1, v/v, pH ¼ 7.20). When 50 equiv. various anions (F , Cl , emission intensity at 512 nm of sensor PW enhanced 11-fold on
ꢀ ꢀ ꢀ ꢀ ꢀ ꢀ ꢀ ꢀ ꢀ
Br , I , AcO , H PO , HSO , ClO , SCN and CN ) were changing the concentration of CN from 0 equiv. to 37.5 equiv.
2
4
4
4
ꢀ
5
respectively added to the solution of PW (2.0 ꢁ 10 M), only Furthermore, the uorescence detection limits of PW towards
ꢀ
ꢀ
CN was found to induce a dramatic color change from color- CN based on 3S /S (where S is the standard deviation of the
B
B
less to yellow. In the corresponding UV-Vis spectra, a dramatic blank solution and S is the slope of the calibration curve) was
absorption band was appeared. However, other examined
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
anions (F , Cl , Br , I , AcO , H
2
PO
4
, HSO
4
, ClO
4
and
ꢀ
SCN ) didn't induce any dramatic changes in color and
absorption spectra (Fig. 2). These results suggested that PW
ꢀ
could recognize CN over all other anions.
Free PW alone exhibited a weak uorescence emission band
at 512 nm when excited at 320 nm in DMSO/H O (1 : 1, v/v, pH
2
ꢀ
¼
7.20), up addition of 50 equiv. CN to the solution of PW
ꢀ
5
(
2.0 ꢁ 10 M), PW induced a signicant uorescence ‘off-on’
ꢀ
response for CN at 512 nm, as shown in Fig. 3, which
responded with a color change from saffron yellow to bright
ꢀ
ꢀ
ꢀ
ꢀ
green under UV lamp. However, other anions (F , Cl , Br , I ,
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
AcO , H PO , HSO4 , ClO4 and SCN ) hardly changed the
2
4
color and uorescence intensity of PW, which indicated that PW
ꢀ
could sense CN with single selectivity in DMSO/H O (1 : 1, v/v,
2
pH ¼ 7.20) solution.
To validate anti-interference capability of sensor PW, PW
ꢀ
Fig. 7 Benesi–Hilderbrand plot of PW with CN .
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
ꢀ
4
,
containing various anions (F , Cl , Br , I , AcO , H
2
PO
ꢀ ꢀ
ꢀ
HSO , ClO
4 4
and SCN ) were investigated by UV-Vis spec-
troscopy and uorescence spectroscopy. Results suggested that
PW solutions with various anions didn't induce distinct spec-
ꢀ
trum changes in absence of CN , however, upon addition of
ꢀ
CN , as shown in Fig. 4, all solutions showed obviously spec-
trum changes, which indicated that sensor PW had an excellent
ꢀ
selectivity for CN over other anions no matter in UV-Vis
spectroscopy and uorescence spectroscopy.
Furthermore, we calculated the quantum yields of PW and
ꢀ
PW + CN by measuring respectively the UV-Vis absorption
spectra and the uorescent spectra and the reference
compound. The quantum yields were calculated using the
40
following equation:
F
F
1
2
A
2
1
41
¼ 4 ꢁ
ꢁ
2
A
Fig. 8 The reversible and reproducible fluorometric switch controlled
by alternating addition of H and CN .
ꢀ
(
where 4
1
is the quantum yield of PW and PW + CN . 4
2
is the
+
ꢀ
quantum yield of reference compound (quinine sulfate, 4 ¼
2
ꢀ
0
.55). F is the uorescent integral of PW and PW + CN . F is
1
2
the uorescent integral of reference compound. A is the
1
ꢀ
absorbance of PW and PW + CN . A
2
is the absorbance of
reference compound). The quantum yield of PW and PW + CN
ꢀ
were 0.0434 M and 0.8916 respectively.
ꢀ
To get insight into the CN (0.01 M) sensing property of
sensor PW, the UV-Vis absorption spectrum and uorescence
spectrum changes of PW were carried out in DMSO/H O (1 : 1,
2
v/v, pH ¼ 7.20) solution. As shown in Fig. 5a, along with the
ꢀ
increasing amount of CN from 0 equiv. to 23 equiv., the
absorption band at 320 nm decreased while the absorption
band at 380 nm increased. At the same time, the well-dened
isosbestic point appeared at 358 nm, which clearly indicated
an interconversion into single discrete chemical species during
the titration process. Fig. 5b showed the emission spectrum
ꢀ
changes on addition of CN , when excited at 320 nm, the
ꢀ
Fig. 9 Job plots of PW and CN .
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down to 1.592 ꢁ 10ꢀ M (Fig. 6), which indicated that PW could by H NMR titration and mass spectrometry. As shown in
7
1
ꢀ
detect low concentration of CN in practical application.
Fig. 10, sensor PW showed two strong peaks at 11.74 ppm and
The association constants (K ) were determined based on the 9.49 ppm in DMSO-d , which correspond to the proton of –OH
a
6
ꢀ

uorescent titration curve using the equation as follows: where and N]CH, upon the addition of 2.5 equiv. CN , the –OH peak
ꢀ
F
1
and F
0
respectively represent the uorescent intensity of host at 11.74 ppm disappeared, which indicated that CN took the
in the presence and absence of ions, Fmax is the saturated protons of –OH due to strong acid was readily deprotonated
intensity of host in the presence of excess amounts of ions; [C] is when basic ions existed, furthermore, we found that the peak of
4
1
the concentration of ions added.
N]CH gradually decreased and showed upeld shi, which
indicated that the deprotonation of hydroxyl made sensor PW
shielded by the increase of electron density through charge
2
1
/(Fmax ꢀ F ) ¼ 1/(F ꢀ F )(1/(K[C] ) + 1)
0
1
0
delocalization in the conjugated system. Aerwards, addition of
+
3
.0 equiv. H to the above system, we found that there appeared
According for formula above, as shown in Fig. 7, the acid
two new peaks at 11.74 ppm and 9.49 ppm, which can be
attributed to the –NH and –OH.
7
reaction equilibrium constant (K
a
) is 2.67 ꢁ 10 , and pK ¼ 6.52.
a
Since pH may affect the charge distribution of PW and
change its inherent uorescence properties, the impact of pH
on PW was studied by uorescence spectroscopy. As shown in
Fig. S1,† sensor PW showed a signicant uorescence response
ESI-MS also gave a strong support for the mechanism of PW
ꢀ
towards CN , as shown in Fig. S3,† PW ion peak was detected at
+
+
m/z 643.2830 (PW + H ), but it appeared at m/z 665.3495 (PW–H
+
+
+
ꢀ
Na + H ) aer the addition of CN (Fig. S4†), which indicated
ꢀ
for CN within the basic pH range from 7.0 and 9.0, indicating
clearly that pH had a signicant inuence on the recognition of
that PW did undergo deprotonation process.
ꢀ
CN .
The reversibility of sensor PW was measured by alternating
+
ꢀ
addition of H and CN in DMSO/H
2
O (1 : 1, v/v, pH ¼ 7.20)
+
solution. As shown in Fig. 8, upon addition of H to the PW–
CN system, the uorescence intensity clearly showed “OFF”
ꢀ
behavior through the regeneration of PW. On further addition
ꢀ
of CN , the uorescence intensity showed “ON” through the
deprotonation of PW. This indicated that sensor PW showed an
ꢀ
excellent reversibility for CN ions, and the “OFF-ON-OFF”
switching process could be repeated more than seven times
without larger uorescence loss.
ꢀ
To conrm the binding stoichiometry between PW and CN ,
the method of continuous variations was used as shown in
Fig. 9. A job plot was implemented, as we expected, the results
ꢀ
demonstrated that a stoichiometry for PW–CN was 1 : 1.
ꢀ
The recognition mechanism of sensor PW towards CN
Fig. 11 The DFT computed HOMO and LUMO diagram of PW and
PW–CN system.
based on the deprotonation of hydroxyl was nally investigated
ꢀ
1
ꢀ
Fig. 10 H NMR spectra of free PW (DMSO-d
6
) and in the presence of different amounts of CN (0.1 M, DMSO-d
6
).
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ꢀ
Scheme 2 A possible mechanism of PW and CN .
ꢀ
Further analysis of the mechanism of PW with CN , we
performed DFT calculations done at the B3LYP/6-311g (2d, p)
34
level of theory. As shown in Fig. 11, the HOMO–LUMO energy
ꢀ
band gap of PW and PW–CN system were respectively 0.12792
a.u. and 0.10447 a.u. Obviously, the HOMO–LUMO energy band
ꢀ
gap of PW was higher than the PW–CN system, which showed
the reaction could occur in dynamics. Furthermore, we could
observe that the electron cloud density of the HOMO levels of
PW are almost localized on the ring of rhodamine B, upon
ꢀ
interaction with CN , the electron cloud of the HOMO levels of
PW shied the ring of coumarin, which clearly indicated that
ꢀ
the addition of CN made sensor PW occur intramolecular
charge transfer (ICT).
Fig. 13 Fluorescence spectra response of PW (20 mM) in diluted bitter
This deprotonation caused an obvious change in absorption almond.
spectra, and the uorescence enhancement at 512 nm was
possibly caused by a large charge separation resulting in
a strong intramolecular charge transfer (ICT) in PW, simulta- strip changed from bisque to dark yellow under visible light,
ꢀ
neously, we also conrmed that the stoichiometry of PW–CN
and changed from ecru to green under UV lamp. This clearly
was 1 : 1. Based on the above ndings, we proposed that indicated that test strips containing PW could act as a practical
ꢀ
ꢀ
a possible interaction mechanism between PW and CN in this colorimetric tool to detect CN .
system which may proceed through the route depicted in
Scheme 2.
To further investigate the practical application of sensor PW
in our lives, we utilized it to detect CN in the bitter almond. 25 g
ꢀ
To facilitate the use of PW for the detection of cyanide in of crushed bitter almond were put into a round ask containing
practical application, test strips were prepared by immersing 100 ml of water and 0.5 g of NaOH, the mixture solution was

lter papers into the DMSO solution of PW (0.01 M) and then stirred for 20 min before ltrating. Then the ltrate was adjusted
drying in air. As shown in Fig. 12, interestingly, the color of test to pH ¼ 9 with fresh double water, and the solution (2.0 ml) was
ꢀ5
added to the solution of PW (0.5 ml, 1.0 ꢁ 10 M), we found
that the uorescence intensity of PW remarkably enhanced,
which clearly indicated that PW could be applied successfully for
ꢀ
detecting CN in bitter almond (Fig. 13).
To further show excellent properties of PW, we also
compared detection limits, solvent medium, and applications
of reported sensors with compound PW, as shown in Table S1.†
4. Conclusion
In summary, we have designed and synthesized a novel che-
ꢀ
mosensor PW, which showed a dual-channel response for CN
ꢀ
in DMSO/H O (1 : 1, v/v) solution within the basic pH range (pH
2
Fig. 12 Photographs of test strips (a) only PW; (b) PW with CN by
ꢀ
¼
7.0–9.0). The uorescence process could be reversed by adding
H and CN , and the switching process could be repeated more
naked eyes; (c) only PW under UV lamp; (d) PW with CN under UV
+
ꢀ
lamp.
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than seven times without a large uorescence loss. Moreover, 16 P. Li, H. Wang, M. Zhang, G. X. Zhang and D. Q. Zhu, Org.
the detection limit on uorescence response of the sensor PW to Lett., 2009, 11, 1943–1946.
CN was down to 1.592 ꢁ 10 M by titration method, which is 17 C. Chen, R. Y. Wang, L. Q. Guo and N. Y. Fu, Org. Lett., 2011,
ꢀ
ꢀ7
ꢀ
6
lower than the maximum level of 1.9 ꢁ 10 M for cyanide in
13, 1162–1172.
drinking water according to WHO guidelines. Notably, the 18 G. Y. Gao, W. J. Qu, B. B. Shi, P. Zhang, Q. Lin, H. Yao,
simple and efficient sensor PW was successfully used to the
qualitative detection of cyanide in bitter almond. Test trips
W. L. Yang, Y. M. Zhang and T. B. Wei, Spectrochim. Acta,
Part A, 2014, 121, 514–613.
based on sensor PW were fabricated and could serve as a prac- 19 D. Shan, C. Mousty and S. Cosnier, Anal. Chem., 2004, 6, 178–
ꢀ
tical colorimetric tool to detect CN in eld measurements. On
182.
ꢀ
account of those advantages, we believe that PW as a CN sensor 20 G. Y. Gao, B. Gong, W. T. Zhang, Q. L. Ye, J. Wei and
makes it more conspicuous for its potential application.
G. L. Ning, Spectrochim. Acta, Part B, 2012, 162, 391–412.
1 T. K. Ghorpade, M. Patri and S. P. Mishra, Spectrochim. Acta,
Part B, 2016, 225, 428–435.
2
Conflicts of interest
22 S. Chattaraj and A. K. Das, Analyst, 1991, 116, 739–741.
There are no conicts to declare.
23 S. Yen, C. T. Wang and J. S. Wang, Chem. Eng. Commun.,
991, 109, 167–180.
1
2
2
2
2
2
2
3
3
3
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3
3
3
3
3
4 W. K. Dong, X. L. Li, L. Wang, Y. Zhang and Y. J. Ding,
Spectrochim. Acta, Part B, 2016, 229, 370–378.
5 J. Qi, J. H. Hu, J. J. Chen, Y. Sun and J. B. Li, Curr. Anal.
Chem., 2016, 12, 119–123.
6 J. H. Hu, Y. Sun, J. Qi, P. X. Pei, Q. Lin and Y. M. Zhang, RSC
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7 J. H. Hu, Y. Sun, J. Qi, Q. Lin and T. B. Wei, Spectrochim. Acta,
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8 Y. Sun, J. H. Hu, J. B. Li and J. Qi, Spectrochim. Acta, Part A,
Acknowledgements
We gratefully acknowledge the support of the National Nature
Science Foundation of China (No. 21467012).
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