Fluoride-selective colorimetric sensor based on thiourea binding site and anthraquinone reporter

Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy
Fang-ying WuZhao-jun Ji

Abstract

A structurally simple colorimetric sensor, N-4-nitrobenzene-N'-1'-anthraquinone-thiourea (1), for anions was synthesized and characterized by (1)H NMR, ESI mass and IR methods. In acetonitrile, the addition of F(-) changed 1 solution from colorless to yellow. In the presence of other anions such as CH(3)CO(2)(-), H(2)PO(4)(-), HSO(4)(-) and Cl(-), however, the absorption spectrum of 1 was slightly red shifted with no obvious color changes observed. The association constants of anionic complexes followed the order of F(-)>CH(3)CO(2)(-)>H(2)PO(4)(-)>HSO(4)(-)>Cl(-)>Br(-), which was different from the order of anion basicity. AM1 calculation results indicated that the most stable configuration of 1 existed in the Z-E-conformation with a six-membered ring via intramolecular hydrogen bond. This made thiourea moiety of 1 in an unfavorable conformation to bond with oxygen-anionic substrates such as CH(3)CO(2)(-) and H(2)PO(4)(-), thus leading to a high selectivity and sensitivity for the detection of F(-).

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Citations

Jun 20, 2012·Journal of Fluorescence·Wen YangJianfen Fan
Dec 25, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Xuefang ShangXiufang Xu
May 23, 2012·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Eun-Mi LeeSung-Hoon Kim
Apr 1, 2008·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Mei-Zhen SunWen-Ming Liu
Oct 9, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Jie ShaoHua-Kuan Lin
Aug 28, 2015·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Hu NiuShusen Chen
Mar 17, 2016·Inorganic Chemistry·Marcin Karbarz, Jan Romański
Aug 25, 2016·The Journal of Physical Chemistry. a·Ivana AntolMario Barbatti
Dec 15, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Amrita SarkarArindam Mukherjee
Mar 26, 2014·Chemical Reviews·Ying ZhouJuyoung Yoon

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