4
Tetrahedron Letters
and similar fluorescent intensity at 538 nm (Figures S3,
2.
Eychmuller, A.; Rogach, A. L. Pure Appl. Chem. 2000, 72, 179-
88.
1
Supporting Information). Thus, all above results confirmed that
the fluorescence sensing response of DNS-MBZO to thiophenol
is indeed due to the conversion of DNS-MBZO to HO-MBZO,
accompanied with generating the non-fluorescent by-product.
Consequently, the probable sensing mechanism was postulated:
the fluorescent HO-MBZO was released by the cleavage of
sulfonate in DNS-MBZO mediated by thiophenol, which led to
the enhanced fluorescence signal.
3
4
.
.
Love, J. C.; Estroff, L. A.; Kriebel, J. K.; Nuzzo, R. G.;
Whitesides, G. M. Chem. Rev. 2005, 105, 1103-1170.
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1090-1092.
5
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Munday, R. J. Appl. Toxicol .1985, 5, 402-408.
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7
8
.
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Material safety data sheet of thiophenol from Centers for Disease
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24, 349-360.
To evaluate the practicability of DNS-MBZO, the standard
addition recovery experiments were carried out by determining
thiophenol in real water samples. The results shown in Table 1
were reported as the mean ± standard deviation of triplicate
experiments for thiophenol spiked. The average recovery test was
9.
Liu, X.; Yang, L.; Gao, L.; Chen, W.; Qi, F.; Song, X.
Tetrahedron 2015, 71, 8285-8289.
11, 28
10. Liu, H. W.; Zhang, X. B.; Zhang, J.; Wang, Q. Q.; Hu, X. X.;
performed by using the standard addition method
. The
Wang, P. ; Tan, W. H. Anal. Chem. 2015, 87, 8896-8903.
recoveries of thiophenol ranged from 99% to 109%, which
indicates that the thiophenol in the water samples could be
accurately measured with good recovery when the probe was
applied. Therefore, the newly designed probe provides a simple
and convenient way to determine the content of highly toxic
thiophenols in real water samples.
1
1. Wang, X. Z.; Cao, J.; Zhao, C. C. Org. Biomol. Chem. 2012, 10,
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Table 1. Determination of thiophenol concentrations in water
samples
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1
1
Sample
Thiophenol
spiked
Thiophenol
recovered
Recovery
%)
6. Sun, W; Li, W. H.; Li, J.; Zhang, J. A.; Du, L. P.; Li, M. Y.
(
Tetrahedron Lett. 2012, 53, 2332-2335.
(
μM)
(μM)
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Yuanboyuan
Lake water
0
0.5
1
3
5
not detected
0.54 ± 0.01
1.05 ± 0.02
3.16 ± 0.04
5.12 ± 0.15
8.17 ± 0.11
10.08 ± 0.15
not detected
0.50 ± 0.02
1.09 ± 0.03
2.97 ± 0.09
5.08 ± 0.05
8.25 ± 0.07
10.05 ± 0.13
108
105
105
102
102
101
1
8. Yu, D. H.; Huang, F. H.; Ding, S. S.; Feng, G. Q. Anal. Chem.
015, 86, 8835-8841.
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J.; Lu, J. M. Tetrahedron Lett. 2011, 52, 595-597.
Schoolyard
River water
0
0.5
1
3
5
101
109
99
102
103
100
2
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3
. Conclusions
In summary, we have developed a novel fluorescence probe
DNS-MBZO for highly selective and sensitive detection of
thiophenol against other common analytes in mixed aqueous
medium. The probe exhibited the fastest response toward various
equivalents of PhSH. In response to thiophenol, DNS-MBZO
exhibited 160-fold off-on fluorescence enhancement and
remarkably large Stokes shift. Moreover, the low limit of
detection, good linear relationship and desirable recovery make
this probe suitable for accurately quantitative determination of
thiophenol concentrations in real water samples.
2
2
7. Lin, W. Y.; Yuan, L.; Long, L. L.; Guo, C. H.; Feng, J. B. Adv.
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29. Chen, Y.; Huang, W.; Li, C.; Bo, Z. Macromolecules 2010, 43,
10216-10220
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0. Li, J.; Zhang, C. F.; Yang, S. H.; Yang, W. C.; Yang, G. F. Anal.
Chem., 2014, 8, 3037-3042.
Supplementary Material
Acknowledgments
Supplementary material associate with this article can be
found in the online version at http://dx.doi.org.
This work was supported by Program for Scientific Research
Innovation Team in Colleges and Universities of Shandong
Province.
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References and notes
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