title: A DFT study of pyrrole-isoxazole derivatives as chemosensors for fluoride anion.
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.
authors.affiliation: College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China.
authors.forename: Ruifa
authors.initials: R
authors.lastname: Jin
authors.affiliation: College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China.
authors.forename: Weidong
authors.initials: W
authors.lastname: Sun
authors.affiliation: College of Resource and Environmental, Jilin Agricultural University, Changchun 130118, China.
authors.forename: Shanshan
authors.initials: S
authors.lastname: Tang
mesh_terms: D005456:Fluorescent Dyes / Q000737:chemistry*; D005459:Fluorides / Q000032:analysis*; D007555:Isoxazoles / Q000737:chemistry*; D008958:Models, Molecular; D011758:Pyrroles / Q000737:chemistry*; D011789:Quantum Theory; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013876:Thiophenes / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D007555:Isoxazoles; D011758:Pyrroles; D013876:Thiophenes; D005459:Fluorides
keywords: BSSE (counterpoise) correction; atoms in molecules; chemosensor; intramolecular charge transfer; pyrrole-isoxazole derivatives