A tripodal supramolecular sensor to successively detect picric acid and CN? through guest competitive controlled AIE

Article abstract of DOI:10.1039/c8nj03568g

Efficient detection of explosives (e.g. picric acid) and toxic compounds (e.g. cyanide) is an important task. Herein, we report a simple and efficient method for the selective and sensitive detection of picric acid (PA) and CN^?via a novel guest

Full text of DOI:10.1039/c8nj03568g

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A tripodal supramolecular sensor to successively
À
detect picric acid and CN through guest
Cite this:DOI: 10.1039/c8nj03568g
competitive controlled AIE†
a
a
a
a
a
b
Qi Lin, * Xiao-Wen Guan, Yan-Qing Fan, Jiao Wang, Lu Liu, Juan Liu,
a
a
a
Hong Yao,
You-Ming Zhang
and Tai-Bao Wei
*
Efficient detection of explosives (e.g. picric acid) and toxic compounds (e.g. cyanide) is an important
task. Herein, we report a simple and efficient method for the selective and sensitive detection of picric
À
acid (PA) and CN via a novel guest competitive controlled aggregation-induced emission (AIE) method.
First, a tripodal host compound (TG) based on a tris-naphthalimide derivative was designed and
synthesized. The TG can self-assemble to a supramolecular system and show blue AIE. Then, we
employed the TG-based supramolecular system as a novel supramolecular sensor (S-TG). Interestingly,
S-TG could selectively detect PA through a competitive binding interaction, and the detection limit
À8
(
LOD) of S-TG for PA is 1.19 Â 10 M. In this process, the self-assembly of S-TG was destroyed and a
Received 17th July 2018,
TG and PA complex (TG–PA) was produced, meanwhile, the AIE of S-TG was quenched. More
Accepted 5th December 2018
interestingly, TG–PA could act as a novel supramolecular sensor for the AIE fluorescent ‘turn-on’
À
À
À7
À
detection of CN , and the LOD of TG–PA for CN is 7.45 Â 10 M. Moreover, PA and CN test kits
were prepared by loading S-TG or TG–PA on silica gel plates. These test kits could conveniently and
DOI: 10.1039/c8nj03568g
À
rsc.li/njc
efficiently detect PA or CN with high selectivity and sensitivity.
1
2
and an environmental pollutant. Simultaneously, due to the
high solubility of PA in water, it easily contaminates soil and
Introduction
The selective and sensitive detection of explosives has attracted ground water upon exposure. Therefore, the detection of PA to
increasing attention because it is very important in homeland avert life safety threats and environmental pollution has been a
1
–3
security and environmental protection. Common explosives matter of concern for scientists. To date, many chemosensors
1
3,14
are based on nitroaromatic compounds (NACs), such as 2,4,6- such as metal organic frameworks (MOFs),
trinitrophenol (picric acid (PA)), 2,4,6-trinitrotoluene (TNT), organic frameworks (SOFs), polymers,
supramolecular
1
5
16,17
18–20
optical sensors,
nitrotoluene (NT), 1,3-dinitrobenzene (DNB), nitrobenzene and so on have been reported for the detection of PA. Among
4
(
NB), etc. However, among various NACs, PA is a widely used them, optical sensors are attracting attention for the detection of
explosive because it shows superior explosive power compared nitroaromatics owing to their high selectivity and sensitivity,
5
,6
to TNT. Moreover, PA is an important fine chemical and inexpensive nature, rapid response and real-time feasibility in
7
–10
21–25
often used in dye industries, pharmaceuticals, and so on.
However, because PA could cause adverse health effects such as the detection of nitroaromatics are available,
anemia, kidney damage, skin irritation, respiratory system challenge to develop effective and easy-to-make chemosensors
solution.
However, although a large number of reports for
2
6–29
it is still a big
1
1
damage and so on, PA is also considered as a toxic compound for convenient detection of PA.
30
In addition, because of the extreme toxicity of cyanide and the
continuing environmental concern caused by its widespread
industrial use, the highly sensitive and selective detection of
cyanide in biological and environmental samples by simple
methods has become a very important and challenging task.
Many methods, such as electrochemical,
polarography, flow injection amperometric,
graphic methods, have been utilized for the detection of CN .
However, among these methods, the fluorimetric technique is a
a
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: linqi2004@126.com,
weitaibao@126.com
3
1
32–34
3
5
36
fluorimetric,
b
College of Chemical Engineering, Northwest University for Nationalities, Lanzhou,
37
38,39
and chromato-
7
30070, China
4
0
À
†
Electronic supplementary information (ESI) available: Complete experimental
procedures and some of the spectroscopic techniques. See DOI: 10.1039/
c8nj03568g
3
6
highly sensitive, easy, and cheap detection methodology.
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Since the concept of aggregation-induced emission (AIE) was
NJC
4
1
proposed by Tang and co-workers in 2001, fluorescent sensors
based on AIE fluorophores (AIEgens) have become a hot spot
4
2–45
because of their unique photophysical properties.
A variety
of chemosensors based on AIE fluorophores such as tetra-
phenylethylene (TPE), silole derivatives, diphenylfumaronitrile
46
derivatives, naphthalimide derivatives, etc., have been reported,
which provide a novel broad platform for the development of AIE-
based chemosensors to efficiently detect explosives or toxic
compounds. However, to the best of our knowledge, reports on
À
AIE-based chemosensors for effective detection of PA or CN are
very scarce.
In view of this and as part of our research interest in sensors
4
7–50
and molecular recognition,
herein, we report a simple and
efficient method for the selective and sensitive detection of
À
PA and CN through rationally introducing guest competitive
controlled aggregation-induced emission (AIE) into a tris-
naphthalimide derivative-based supramolecular sensor. The
strategies for the design of the tris-naphthalimide derivative
are as follows. First, the naphthalimide moiety acts as the p–p
interaction site as well as the fluorescent signal group. Second,
an amido group was introduced as the hydrogen bonding site.
Fortunately, the tripodal host compound (TG) based on a tris-
naphthalimide derivative could self-assemble to a supramole-
cular system in DMSO solution and shows aggregation-induced
emission (AIE). Then, we employed the TG-based supramole-
cular system as a supramolecular sensor (S-TG). Interestingly,
S-TG could selectively detect PA through competitive binding
interactions. In this process, the self-assembly of S-TG was
destroyed and a TG and PA complex (TG–PA) was produced,
meanwhile, the AIE of S-TG was quenched. More interestingly,
the complex TG–PA could act as a novel supramolecular sensor
À
for the AIE fluorescent ‘turn-on’ detection of CN with high
selectivity and sensitivity.
Fig. 1 (a) The structure of TG and the possible recognition mechanism for
À
successively monitoring PA and CN ; (b) photo showing the Tyndall effect
À
of S-TG, TG–PA and TG–PA + CN ; SEM images of (c) TG and (d) S-TG.
Results and discussion
The novel tripodal compound TG was synthesized by rationally
connecting trimesoyl chloride with N-(4-(amino)-phenyl)-
naphthalimide (DN) through the formation of three amido bonds
(Scheme S1, ESI†). Interestingly, TG shows blue aggregation-
induced emission (AIE) in DMSO solution at lem = 435 nm. This
fluorescence has been confirmed as AIE through concentration-
dependent fluorescence spectroscopy, the Tyndall phenomenon
1
and concentration-dependent H NMR spectroscopy. In the
concentration-dependent fluorescence spectra (Fig. S6, ESI†),
À5
when the TG concentration reached 1 Â 10 M, the emission
intensity at 435 nm showed a sudden increase and the solution
emitted blue fluorescence. Meanwhile, as shown in Fig. 1b,
TG could dissolve in DMSO and exhibited a clear Tyndall effect.
In the concentration-dependent H NMR spectra of TG (Fig. 2),
with increasing TG concentration, the signals of the proton H2
1
1
Fig. 2 Partial H NMR spectra of TG in DMSO-d
6
at various concentra-
tions: (a) 5.0; (b) 10; (c) 20; (d) 30; (e) 40; (f) 50 mM.
on the amido groups exhibited downfield shifts, which indi-
cated that H2 (–NH) formed stable intermolecular hydrogen Meanwhile, the signals of the protons H4, H5, H6 and H7
bonds of –N–HÁ Á ÁOQC– with –CQO on adjacent molecules. on the naphthalimide group showed obvious upfield shifts,
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which suggested that the naphthalimide group was involved
5
1
in the self-assembly process by p–p stacking interactions.
According to the above results, the proposed self-assembly
mechanism of TG is shown in Fig. 1a; TG self-assembled to a
supramolecular system (S-TG) through p–p and hydrogen bond
interactions and showed aggregation-induced emission (AIE).
As shown in Fig. 1c and d, using SEM, TG exhibits an irregular
powder structure (Fig. 1c), while TG self-assembled to supra-
molecular S-TG showing graceful uniform fibres (Fig. 1d); this
result also showed that TG formed the supramolecular polymer
S-TG by supramolecular interactions.
We employed the TG-based supramolecular system as a
novel supramolecular sensor, S-TG, to detect NACs. The NAC
response properties of the sensor S-TG were investigated by
adding various NACs including picric acid (PA), 4-nitroaniline,
4
2
-nitrotoluene, 2,4-dinitrofluorobenzene, 4-nitrochlorobenzene,
-nitrochlorobenzene, 3-nitrochlorobenzene, 2,4-dinitrochloro-
benzene, 3-nitrobromobenzene, 1,3-dinitrobenzene, nitrobenzene,
4-nitroacetophenone, 3-nitrobenzaldehyde, 4-nitrobenzaldehyde,
2
-nitrobenzoic acid, 3-nitrobenzoic acid, and 4-nitrobenzoic acid
À4
into a DMSO solution of S-TG (c = 1.0 Â 10 M). Interestingly,
S-TG displayed a very strong emission peak (lem = 435 nm) in
the corresponding fluorescence spectra. However, after adding
10.0 equivalents of different NACs into the S-TG solutions, only
PA caused the quenching of the fluorescence of TG (Fig. 3a and
Fig. S7, ESI†). Simultaneously, a color change from colorless to
yellow was observed by the naked eye upon the addition of PA to Fig. 3 (a) Fluorescence emission of the S-TG (1.0 Â 10À4 M) in the
sensor S-TG, in agreement with the appearance of a new presence of different nitroaromatics (0.01 M); (b) absorbance spectra of
À4
the S-TG (1.0 Â 10 M) in the presence of different nitroaromatics (0.01 M)
absorption band at about 375 nm in the corresponding UV-vis
spectrum (Fig. 3b). However, other examined NACs did not cause
any similar response. These results suggested that the sensor
S-TG displayed excellent selectivity to PA over all other NACs.
As we all know, selectivity and sensitivity are important
features for chemosensors. Therefore, we carefully investigated
the specific selectivity of the sensor S-TG to PA over other
miscellaneous competitive NACs by competitive experiments.
As shown in Fig. 4, PA still produced a similar fluorescence
emission response in the presence of other NACs. Moreover,
similar competitive experiments were also carried out to study
the selective recognition of S-TG for PA via UV-vis spectroscopy
in DMSO solution.
(
Fig. 5). The results indicated that miscellaneous competitive
À4
NACs did not lead to any significant interference in the PA Fig. 4 Fluorescence intensity response of the S-TG (1.0 Â 10 M) and PA
(
10 equiv.) in the presence of various nitroaromatics in DMSO solution.
sensing process. Therefore, sensor S-TG could be used as a
fluorescent and colorimetric dual-channel sensor for the detec-
tion of PA.
In order to evaluate S-TG for the detection sensitivity of PA,
the emission and absorption spectra of sensor S-TG were moni-
tored during titration with different concentrations of PA. As
shown in Fig. S8 (ESI†), with increasing amounts of PA, a gradual
decrease in the emission intensity of S-TG at 435 nm was
observed. Simultaneously, as shown in Fig. S9 (ESI†), approxi-
mately 99.2% fluorescence emission quenching was observed
upon the addition of 10.0 equivalents of PA. Correspondingly,
in the absorption spectra (Fig. S10, ESI†), upon successive
addition of 0–14 equivalents of PA to a DMSO solution of
À4
Fig. 5 Absorption intensity response of S-TG (1.0 Â 10
M) and PA
S-TG, a new absorption peak at 375 nm gradually increased. (10 equiv.) in the presence of various nitroaromatics in DMSO solution.
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Finally, the detection limit of S-TG for PA determined by the
Interestingly, the complex TG–PA could be employed as
emission and absorption spectroscopy titrations and calculated a novel supramolecular sensor for the fluorescent ‘‘turn-on’’
5
2
À8
À
on the basis of the 3s/s method was 1.19 Â 10 M and 1.38 Â detection of CN . The anion response properties of TG–PA were
À8
10
M, respectively (Fig. S11 and S12, ESI†).
Moreover, the fluorescence emission response of S-TG to PA anions (AcO , H PO , HSO4 , ClO4 , F , Cl , Br , I , SCN
was analyzed by the linear part of the Stern–Volmer equation:
carefully investigated by adding various water solutions of
À
À
4
À
À
À
À
À
À
À
2
1
9
À
À4
and CN ) into the DMSO solution of TG–PA (c = 1.0 Â 10 M).
I
0
/I = 1 + KSV [Q], where I
0
is the initial fluorescence intensity of TG–PA exhibits negligible fluorescence emission, while with
À
TG before the addition of PA, I is the fluorescence intensity after the gradual addition of CN , the TG–PA solution shows a
the addition of PA, [Q] is the molar concentration of PA, and KSV gradual increase of the emission intensity at 450 nm (Fig. 7a).
À1
is the quenching constant (M ). The Stern–Volmer plots for PA Meanwhile, a bright blue fluorescence could be distinguished
2
are nearly linear at low concentrations (R = 0.99405) and the by the naked eye under a UV-lamp (365 nm) as shown in Fig. 7a.
4
À1
constant KSV for PA was found to be 7.40 Â 10 M (Fig. 6). In comparison, the addition of various other anions such
À
À
4
À
À
À
À
À
À
À
In addition, a comprehensive comparison of TG with some as AcO , H PO , HSO4 , ClO4 , F , Cl , Br , I and SCN
2
reported materials for the detection for PA is listed in Table S1 to the solution of TG–PA showed very slight changes. These
(
ESI†), which indicated that S-TG has a more sensitive response results clearly suggested that sensor TG–PA exhibited high
À
ability to PA than most reported sensors.
selectivity to CN over other anions.
The recognition mechanism of S-TG for PA was carefully
Then, competitive experiments were carried out by adding
1
À
investigated via H NMR, FT-IR and ESI-MS spectroscopies. In 60.0 equiv. of a CN water solution and 60.0 equiv. of various
1
the H NMR titration experiments (Fig. S13, ESI†), with the anion water solutions to the TG–PA DMSO solution (c = 1.0 Â
À4
addition of different equivalents of PA into a DMSO-d solution 10
M). The fluorescence selectivity was examined at an
6
À4
of TG (1.0 Â 10 M), all of the aromatic protons (H3–H7) on TG emission wavelength of 450 nm in the presence of other anions,
showed downfield shifts, which indicated that the p–p inter- and showed that all the competing anions did not interfere in
À
actions in the self-assembled supramolecular system of S-TG the detection of CN (Fig. 7b). This result showed the high
were destroyed. Meanwhile, the signals of H2 on the amido group selectivity of the sensor TG–PA toward CN over the other
À
of TG and Hp on PA showed distinct downfield shifts, which analytes mentioned above.
indicated that H2 formed stable intermolecular hydrogen bonds
To further investigate the efficiency of sensor TG–PA toward
À
with –NO on PA molecules. Meanwhile, in the corresponding IR CN detection, we carried out fluorescence titration experiments.
2
spectra (Fig. S14, ESI†), the –NH andQC–H stretching vibration
À1
absorption peaks of TG appeared at 3423 and 2928 cm
respectively; however, in a mixture of TG and PA, the –NH and
QC–H stretching vibration absorption peaks shifted to 3415 and
À1
2
920 cm , which indicated that TG and PA formed stable
intermolecular hydrogen bonds through the –NH on the amido
groups of TG and –NO on PA (Fig. 1a). These results suggested
2
that the addition of PA destroyed the self-assembly of S-TG, which
induced quenching of the AIE of S-TG, meanwhile, a novel host–
guest complex TG–PA was formed. The proposed mechanism was
confirmed by the ESI-MS spectra (Fig. S15, ESI†); when excess
+
PA was added to a solution of TG, a peak for [TG + PA + Na ]
(m/z 1272.2407) was found at 1272.2116, indicating the formation
of the stabilized host–guest complex TG–PA (1 : 1 stoichiometry).
À4
Fig. 7 (a) Fluorescence spectra of TG–PA (1.0 Â 10 M) in DMSO in the
presence of various anions; (b) fluorescence intensity response of TG–PA
(1.0 Â 10À4 M) and CN in the presence of various anions in DMSO solution.
À
Fig. 6 Stern–Volmer plot for PA at a lower concentration.
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As shown in the fluorescence spectrum, addition of increasing
À
amounts of CN ions to the solution of TG–PA directly leads to
the emission ‘turn-on’ (Fig. S16, ESI†). Strikingly, an excellent
2
À
linear dependence (R = 0.98902) of the concentration of CN
was observed. Meanwhile, the detection limit of the fluores-
cence titration spectrum changes calculated on the basis of the
5
2
À7
3
s/s method is 7.45 Â 10 M (Fig. S17, ESI†), indicating the
À
high sensitivity of the sensor to CN .
The recognition mechanism of TG–PA for CN was carefully
investigated via H NMR and IR spectroscopies. As shown in the
À
1
1
À
H NMR spectra (Fig. 8), with increasing CN concentrations,
the signals of the H2 on the amido groups of TG gradually
À
disappeared; this result indicated that CN caused the H2 to
undergo a deprotonation process, which broke the intermole-
cular hydrogen bonding between TG and PA and caused the
destruction of the sensor TG–PA complex (Fig. 1). Meanwhile, Hp
on PA showed upfield shifts because of the shielding effect.
Simultaneously, the H4, H5, H6 and H7 protons showed slight
upfield shifts, which indicated that TG recovered its self-
assembly by p–p interactions, meanwhile, the AIE of S-TG was
recovered (Fig. 1). To further understand the process, FT-IR
spectroscopy of TG was carried out (Fig. S14, ESI†); the –NH
and QC–H stretching vibration absorption peaks of TG–PA
Fig. 9 (a) Photographs of the paper test strips of probe TG under UV light
(
365 nm) and (b) solid state emission spectra of TG with the addition of
different concentrations of PA.
spectra (Fig. 9b), along with the increasing amounts of PA, the
emission intensity of TG showed a gradual decrease.
Subsequently, to investigate the practical applications of
À
TG–PA, CN test kits were prepared by loading TG–PA on silica
À1
À
appeared at 3415 and 2920 cm , respectively, when CN was
added to a solution of the TG–PA complex, and the stretching
vibration absorption peaks of –NH disappeared, meanwhile the
gel plates. Test kits containing TG–PA were utilized to detect
À
À
CN . As shown in Fig. S18 (ESI†), when CN water solution was
added to the test kits, a fluorescence turn on response can be
observed under a 365 nm UV-lamp. In order to investigate the
practical applications of the sensor TG–PA for the detection of
À1
QC–H absorption peaks shifted to 2930 cm . These results also
support the above-mentioned proposed mechanism.
In order to investigate the application of sensor S-TG for the
convenient detection of PA, a PA test kit was prepared by
loading S-TG on a silica gel plate. The test kit exhibits a bright
blue fluorescence emission. As shown in Fig. 9a, upon the
addition of a solution of PA, we found that the silica gel plate-
based PA test kit showed distinct fluorescence quenching. The
À
32
CN , we employed peach seeds as a practical sample. The
experiments were carried out as follows: 50 grams of peach
seeds was crushed and pulverized, and then, 200 mL of water
was added to the pulverized peach seeds, and the resulting
turbid solution was vigorously stirred for 30 min. After this,
results indicated that the detection limit of PA was 1.0 Â
À8
10
M. Therefore, the S-TG-based silica gel plates could act
as a novel and efficient test kit for convenient detection of PA in
solution. Meanwhile, in the corresponding solid state emission
1
À4
Fig. 8 Partial H NMR spectra of TG and PA (1 : 1) in DMSO-d
6
with
Fig. 10 (a) Fluorescence spectra of TG–PA (1.0 Â 10 M) in the presence
À
different equivalents of CN : (a) 0; (b) 0.2; (c) 0.4; (d) 0.6; (e) 0.8; (f) 1.0;
of two different cyanide solutions in DMSO (lex = 370 nm); (b) response
photographs of TG–PA in wild peach seeds and standard solution of CN .
À
(g) 2.0; (h) 3.0.
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the turbid solution was filtered and a practical sample solution
was obtained. As shown in Fig. 10a, upon the addition of
7 S. S. Nagarkar, B. Joarder, A. K. Chaudhari, S. Mukherjee
and S. K. Ghosh, Angew. Chem., Int. Ed., 2013, 52, 2881.
8 J. Shen, J. Zhang, Y. Zuo, L. Wang, X. Sun, J. Li, W. Han and
R. He, J. Hazard. Mater., 2009, 163, 1199.
9 Y. Ma, S. Huang, M. Deng and L. Wang, ACS Appl. Mater.
Interfaces, 2014, 6, 7790.
À4
the practical sample solution into TG–PA (1.0 Â 10 M), the
fluorescence intensity of sensor TG–PA increased rapidly. The
bright blue fluorescence could be distinguished by the naked
eye under a UV lamp (365 nm), as shown in Fig. 10b. These
results indicated that sensor TG–PA could efficiently detect 10 A. Ding, L. M. Yang, Y. Y. Zhang, G. B. Zhang, L. Kong, X. J.
À
CN through fluorescent ‘‘turn-on’’ in a practical sample.
Zhang, Y. P. Tian, X. T. Tao and J. X. Yang, Chem. – Eur. J.,
014, 20, 12215.
2
1
1
1
1 K. M. Wollin and H. H. Dieter, Arch. Environ. Contam.
Toxicol., 2005, 49, 18.
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X. Meng, L.-L. Wu and H.-J. Zhang, Adv. Funct. Mater., 2014,
Conclusions
In summary, a tripodal host compound TG based on a tris-
naphthalimide derivative was designed and synthesized. The
TG could self-assemble to a supramolecular system (S-TG) and
show aggregation-induced emission (AIE). Interestingly, S-TG
could selectively and sensitively detect picric acid (PA). More-
over, TG could form a stable TG–PA complex and act as a novel
supramolecular sensor for the fluorescence ‘‘turn-on’’ detection of
24, 4034.
1
4 Y. Takashima, V. M. Martinez, S. Furukawa, M. Kondo,
S. Shimomura, H. Uehara, M. Nakahama, K. Sugimoto
and S. Kitagawa, Nat. Commun., 2011, 2, 168.
À
À
CN . The recognition mechanism of S-TG for PA and TG–PA for
15 Y. Zhang, T. G. Zhan, T. Y. Zhou, Q. Y. Qi, X. N. Xu and
CN is based on a novel guest competitive controlled aggregation-
X. Zhao, Chem. Commun., 2016, 52, 7588.
induced emission (AIE) process. Meanwhile, test kits based on
1
6 A. S. G. Liu, D. Luo, N. Li, W. Zhang, J. L. Lei, N. B. Li and
H. Q. Luo, ACS Appl. Mater. Interfaces, 2016, 8, 21700.
7 S. Shanmugaraju, C. Dabadie, K. Byrne, A. J. Savyasachi,
D. Umadevi, W. Schmitt, J. A. Kitchen and T. Gunnlaugsson,
Chem. Sci., 2017, 8, 1535.
S-TG and TG–PA for convenient fluorescence detection of PA and
À
À
CN were prepared. Moreover, TG–PA can detect CN through
fluorescence in a practical sample. It is worth mentioning that
the novel recognition mechanism based on the guest competi-
tive controlled aggregation-induced emission (AIE) process pro-
vides a new way for the design of fluorescent sensors.
1
1
8 V. Bhalla, A. Gupta and M. Kumar, Org. Lett., 2012, 14,
3112.
1
9 M. C. Rong, L. P. Lin, X. H. Song, T. T. Zhao, Y. X. Zhong,
J. W. Yan, Y. R. Wang and X. Chen, Anal. Chem., 2015,
Conflicts of interest
8
7, 1288.
0 B. Gogoi and N. S. Sarma, ACS Appl. Mater. Interfaces, 2015,
, 11195.
There are no conflicts to declare.
2
7
Acknowledgements
21 S. Hussain, A. H. Malik, M. A. Afroz and P. K. Iyer, Chem.
Commun., 2015, 51, 7207.
This work was supported by the National Natural Science
Foundation of China (NSFC) (No. 21574104; 21662031; and
2
2
2
2
2 V. Bereau, C. Duhayon and J. P. Sutter, Chem. Commun.,
2014, 50, 12061.
21661028) and the Program for Changjiang Scholars and Inno-
3 D. Dinda, A. Gupta, B. K. Shaw, S. Sadhu and S. K. Saha, ACS
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4 K. K. Kartha, S. S. Babu, S. Srinivasan and A. Ajayaghosh,
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5 S. S. Nagarkar, B. Joarder, A. K. Chaudhari, S. Mukherjee
and S. K. Ghosh, Angew. Chem., Int. Ed., 2013, 52, 2881.
vative Research Team in the University of Ministry of Education
of China (IRT 15R56).
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