Organic & Biomolecular Chemistry
Paper
Table 1 Analysis of thiophenol concentrations in real water samples
Notes and references
PhSH spiked
(μM)
PhSH recovered
(μM)
Recovery
(%)
1
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Sample
1
Saône River
water
0
1.00
Not detected
0.97 + 0.09
1.84 + 0.12
2.86 + 0.11
0
2
97
92
95
2
3
.00
.00
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Rhône River
water
0
1.00
Not detected
1.05 + 0.06
2.06 + 0.08
3.07 + 0.14
0
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105
103
102
2
3
.00
.00
Conditions: The glyco-probe self-assembled from TD-1 (10 μM) and
TPE2S (10 mM) responded to thiophenol in 95% water samples with
THF after 5 min.
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(
0
0–3 μM). The fluorescence increase (I − I ) was similar to the
results measured in PBS solution (Fig. S10, ESI†). We have also
injected exogenously known concentrations of thiophenol
0–3 μM) into the real water samples (Table 1). The fluo-
1233–1237.
(
T. Wang, E. Chamberlain, H. Shi, C. D. Adams and Y. Ma,
rescence signal recovery was always found to be near 100%
from the expected intensities through analysis using the titra-
tion curve. Therefore, the self-assembled glyco-probe between
TPE2S and TD-1 could be used for thiophenol quantification
in real water samples.
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1
1
1
1
1
1
1
1
1
1
2
Conclusion
In summary, the detection of thiophenol is of interest as this
toxic compound can pollute drinking water or water used for
recreation. The design of a new fluorescent probe with a reac-
tive 2,4-dinitrosulfonate moiety was achieved by the conju-
gation between a TPE AIEgen and a DCM core. The resulting
probe could react with thiophenol to release a phenol group
on the TPE-DCM moiety, thus enhancing the fluorescence
emission at 570 nm. Nevertheless, the poor water solubility of
the resulting phenol did not allow stable measurements. We
thus proposed a self-assembly strategy with water-soluble TPE-
based glycoclusters, leading to a new glyco-probe for the quan-
titative and selective detection of thiophenol in PBS solution
as well as environmental water samples.
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Conflicts of interest
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2
2
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5
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Acknowledgements
7
The authors are thankful for the financial support from the 23 W. Jiang, Y. Cao, Y. Liu and W. Wang, Chem. Commun.,
Natural Science Foundation of China (No. 21788102, 2010, 46, 1944–1946.
1853201, 21722801 and 21776078) and the Shanghai 24 M. Zhang, T. Leng, Y. Shen and C. Wang, Analyst, 2018,
9
Municipal Science and Technology Major Project (No.
143, 756–760.
2
018SHZDZX03) and the China Scholarship Council for a PhD 25 Z. Guo, A. Shao and W.-H. Zhu, J. Mater. Chem. C, 2016, 4,
stipend to L. D. (No. 201606740066).
2640–2646.
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