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A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China
College of Resource and Environmental, Jilin Agricultural University, Changchun 130118, China
* Author to whom correspondence should be addressed.
Received: 16 March 2012; in revised form: 5 July 2012 / Accepted: 21 August 2012 / Published: 5 September 2012
Abstract: The interactions between chemosensors, 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4-carboxamide (AIC) derivatives, and different anions (F− Cl−, Br−, AcO−, and H2PO4−) have been theoretically investigated using DFT approaches. It turned out that the unique selectivity of AIC derivatives for F− is ascribed to their ability of deprotonating the host sensors. Frontier molecular orbital (FMO) analyses have shown that the vertical electronic transitions of absorption and emission for the sensing signals are characterized as intramolecular charge transfer (ICT). The study of substituent effects suggests that all the substituted derivatives are expected to be promising candidates for fluoride chemosensors both in UV-vis and fluorescence spectra except for derivative with benzo[d]thieno[3,2-b]thiophene fragment that can serve as ratiometric fluorescent fluoride chemosensor only.
Keywords: pyrrole-isoxazole derivatives; chemosensor; BSSE (counterpoise) correction; intramolecular charge transfer; atoms in molecules
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Jin, R.; Sun, W.; Tang, S. A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion. Int. J. Mol. Sci. 2012, 13, 10986-10999.
Jin R, Sun W, Tang S. A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion. International Journal of Molecular Sciences. 2012; 13(9):10986-10999.
Jin, Ruifa; Sun, Weidong; Tang, Shanshan. 2012. "A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion." Int. J. Mol. Sci. 13, no. 9: 10986-10999.