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Sensors 2015, 15(11), 28166-28176; doi:10.3390/s151128166

The Synthesis and Anion Recognition Property of Symmetrical Chemosensors Involving Thiourea Groups: Theory and Experiments

1
Department of Chemistry, Xinxiang Medical University, Xinxiang 453003, China
2
School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, China
3
Department of Chemistry, Nankai University, Tianjin 300071, China
*
Author to whom correspondence should be addressed.
Academic Editor: W. Rudolf Seitz
Received: 15 October 2015 / Revised: 30 October 2015 / Accepted: 30 October 2015 / Published: 6 November 2015
(This article belongs to the Section Chemical Sensors)
View Full-Text   |   Download PDF [1345 KB, uploaded 6 November 2015]   |  

Abstract

The synthesis of four symmetrical compounds containing urea/thiourea and anthracene/nitrobenzene groups was optimized. N,N’-Di((anthracen-9-yl)-methylene) thio-carbonohydrazide showed sensitive and selective binding ability for acetate ion among the studied anions. The presence of other competitive anions including F, H2PO4, Cl, Br and I did not interfere with the strong binding ability. The mechanism of the host-guest interaction was through multiple hydrogen bonds due to the conformational complementarity and higher basicity. A theoretical investigation explained that intra-molecular hydrogen bonds existed in the compound which could strengthen the anion binding ability. In addition, molecular frontier orbitals in molecular interplay were introduced in order to explain the red-shift phenomenon in the host-guest interaction process. Compounds based on thiourea and anthracene derivatives can thus be used as a chemosensor for detecting acetate ion in environmental and pharmaceutical samples. View Full-Text
Keywords: thiourea derivative; symmetrical structure; chemosensor; theoretical investigation thiourea derivative; symmetrical structure; chemosensor; theoretical investigation
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Shang, X.; Yang, Z.; Fu, J.; Zhao, P.; Xu, X. The Synthesis and Anion Recognition Property of Symmetrical Chemosensors Involving Thiourea Groups: Theory and Experiments. Sensors 2015, 15, 28166-28176.

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