Int. J. Mol. Sci. 2012, 13(9), 10986-10999; doi:10.3390/ijms130910986
Article

A DFT Study of Pyrrole-Isoxazole Derivatives as Chemosensors for Fluoride Anion

1,* email, 1email and 2email
Received: 16 March 2012; in revised form: 5 July 2012 / Accepted: 21 August 2012 / Published: 5 September 2012
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.
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
PDF Full-text Download PDF Full-Text [571 KB, uploaded 19 June 2014 04:25 CEST]

Export to BibTeX |
EndNote


MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert