A Fluorescent Chemosensor for Dihydrogen Phosphate Ion
fluorescent efficiency loss (Figure 7).
4-(diethylamino) phenyl]-1H-imidazo[4,5-b]phenazine
+ +
and Fe3 complex. The sensor GY-Fe3 showed fluo-
rescent selectivity for H2PO−4 . Moreover, this is the
first time that a long wavelength emission fluorescent
chemosensor with high selectivity for H2PO−4 was de-
signed. Thus, it is believed that this receptor will have a
role to play in the sensing, detection, and recognition of
+
H2PO−4 ions. In addition, test strips based on GY-Fe3
were fabricated, which also exhibited a good selectivity
to H2PO−4 as in solution. Thus, we believe that the test
strips could act as test kits which could detect H2PO−4
conveniently and efficiently in solutions.
Acknowledgement
This work was supported by the National Natural
Science Foundation of China (Nos. 21064006,
21262032 and 21161018), the Program for Changjiang
Scholars and Innovative Research Team in University of
Ministry of Education of China (No. IRT1177), the
Natural Science Foundation of Gansu Province (No.
1010RJZA018), the Youth Foundation of Gansu Prov-
ince (No. 2011GS04735) and NWNU-LKQN-11-32.
Figure 7 Emission spectra showing the reversible complexation
+
between GY and Fe3 (5.0 equiv.) by introduction of H2PO−4
(10.0 equiv.).
To investigate the practical application of sensor GY,
test strips were prepared by immersing filter papers into
References
+
+
a solution of GY-Fe3 ([GY]/[Fe3 ]=1∶20, [GY]=2
×10−5 mol/L) and then drying in air. The test strips
[1] (a) Ingale, S. A.; Seela, F. J. Org. Chem. 2012, 77, 9352; (b) Er-
makova, E.; Michalak, J.; Meyer, M.; Arslanov, V.; Tsivadze, A.;
Guilard, R. Org. Lett. 2013, 15, 662; (c) Neupane, L. N.; Park, J. Y.;
Park, J. H.; Lee, K. H. Org. Lett. 2013, 15, 254; (d) Huang, X. B.;
Miao, Q.; Wang, L.; Jiao, J. M.; He, X. J.; Cheng, Y. X. Chin. J.
Chem. 2013, 31, 195; (e) He, X. P.; Xie, J.; Chen, G. R.; Chen, K. X.
Chin. J. Chem. 2012, 30, 2874.
[2] (a) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; (b)
Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 486; (c)
Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Chem. Soc. Rev. 2006,
35, 355.
+
containing GY-Fe3 were utilized to sense H2PO−4
and other anions. As shown in Figure 8, when H2PO−4
and the other anions were added on the test kits, the
obvious color change was observed only with H2PO−4
solution under the 365 nm UV lamp. And potentially
competitive ions exerted no influence on the detection
of H2PO−4 by the test strips. Therefore, the test strips
could detect H2PO−4 conveniently in solutions.
[3] (a) Khatua, S.; Cho, S. H.; Lee, J.; Kim, K. B.; Do, Y. K.; Churchill,
D. G. Inorg. Chem. 2009, 48, 2993; (b) Vicente, M. C.; Burguete, M.
I.; Galindo, F.; Izquierdo, M. A.; Kumar, D. K.; White, A. J. J. Org.
Chem. 2012, 77, 490; (c) Liu, C.; Zhou, Z. G.; Gao, Y.; Yang, H.; Li,
B. G.; Li, F. Y.; Huang, C. H. Sci. China Chem. 2009, 52, 760.
[4] (a) Huang, X. H.; He, Y. B.; Hu, C. G.; Chen, Z. H. Eur. J. Org.
Chem. 2009, 1549; (b) Sessler, J. L.; Lynch, V. J. Am. Chem. Soc.
2006, 128, 16518; (c) Huang, J. L.; Wang, B.; Ye, J. G.; Liu, B.; Qiu,
H. Y.; Yin, S. C. Chin. J. Chem. 2012, 30, 1857; (d) Zhang, L.;
Wang, L. M.; Zhang, G. J.; Yu, J. J.; Cai, X. F.; Teng, M. S.; Wu, Y.
Chin. J. Chem. 2012, 30, 2823.
[5] (a) Li, G.; Wu, Y. C.; Gao, J. K.; Wang, C. Y.; Li, J. B.; Zhang, H. C.
J. Am. Chem. Soc. 2012, 134, 20298; (b) Bahnasawy, A. A. E.; Ah-
wany, M. F. E. Phosphorus Sulfur Silicon Relat. Elem. 2007, 8,
1937.
(a)
(b)
(c)
(d)
+
Figure 8 Photographs of GY-Fe3 on test papers: (a) only
+
GY-Fe3 , (b) after immersion into DMSO solutions with GY-
+
Fe3 - H2PO−4 , (c) after immersion into DMSO solutions with
[6] (a) Zhang, Y. M.; Lin, Q.; Wei, T. B.; Qin, X. P.; Li, Y. Chem.
Commun. 2009, 45, 6074; (b) Shi, B. B.; Zhang, P.; Wei, T. B.; Yao,
H.; Lin, Q.; Zhang, Y. M. Chem. Commun. 2013, 49, 7812; (c) Wei,
T. B.; Zhang, P.; Shi, B. B.; Chen, P.; Lin, Q.; Liu, J.; Zhang, Y. M.
Dyes Pigments 2013, 97, 297; (d) Wu, G. Y.; Shi, B. B.; Hu, B.;
Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Chin. J. Chem. 2014, 32,
637; (e) Zhang, Y. M.; Shi, B. B.; Zhang, P.; Huo, J. Q.; Chen, P.;
Lin, Q.; Liu, J.; Wei, T. B. Sci. China Chem. 2013, 56, 612; (f)
Zhang, P.; Zhang, Y. M.; Lin, Q.; Yao, H.; Wei, T. B. Chin. J. Org.
Chem. 2014, 34, 1300; (g) Zhang, Y. M.; Wang, Y. L.; Lin, Q.;
Wang, D. D.; Wei, T. B. Chin. J. Org. Chem. 2009, 4, 575; (h) Li, J.
others ions, (d) after immersion into DMSO solutions with
H2PO−4 and other ions under irradiation at 365 nm.
Conclusions
In summary, we have presented a long wavelength
+
emission dihydrogen phosphate chemosensor (GY-Fe3 )
according to the excited state intramolecular proton
transfer (ESIPT) mechanism based on a 2-[2-hydroxy-
Chin. J. Chem. 2014, 32, 1238—1244
© 2014 SIOC, CAS, Shanghai, & WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
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