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

Sensors

Xuefang Shang³  Zhenhua Yang³  Jiajia Fu¹  Peipei Zhao¹  Xiufang Xu² 

[1] School of Pharmacy, Xinxiang Medical University, Xinxiang 453003, China; E-Mails:;Department of Chemistry, Nankai University, Tianjin 300071, China; E-Mail:;Department of Chemistry, Xinxiang Medical University, Xinxiang 453003, China; E-Mail:

关键词: thiourea derivative;    symmetrical structure;    chemosensor;    theoretical investigation;   

DOI  :  10.3390/s151128166

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.