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. 2012;13(9):10986-10999.
doi: 10.3390/ijms130910986. Epub 2012 Sep 5.

A DFT study of pyrrole-isoxazole derivatives as chemosensors for fluoride anion

Ruifa Jin  1 , Weidong Sun  1 , Shanshan Tang  2
Affiliations

A DFT study of pyrrole-isoxazole derivatives as chemosensors for fluoride anion

Ruifa Jin et al. Int J Mol Sci. 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 H(2)PO(4) (-)) 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: BSSE (counterpoise) correction; atoms in molecules; chemosensor; intramolecular charge transfer; pyrrole-isoxazole derivatives.

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Figures

Figure 1
Figure 1
Frontier molecular orbital (FMOs) of AIC and AIC− in S0 at the B3LYP/6- 31+G(d,p) level.
Scheme I
Scheme I
Geometries of 3-amino-5-(4,5,6,7-tetrahydro-1H-indol-2-yl)isoxazole-4- carboxamide (AIC) and its derivatives, along with atom numbering.
See this image and copyright information in PMC

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