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Selective anion recognition by inhibition of excited state intramolecular proton transfer process via hydrogen bonding interaction and efficient deprotonation: Spectroscopic and theoretical investigation

Paper ID Volume ID Publish Year Pages File Format Full-Text
27082 43999 2012 9 PDF Available
Title
Selective anion recognition by inhibition of excited state intramolecular proton transfer process via hydrogen bonding interaction and efficient deprotonation: Spectroscopic and theoretical investigation
Abstract

Anion (X) recognition fluorescent chemosensor 5-(4-Fluoro-phenyl)-2-hydroxy-nicotinonitrile (FP2HN) having both –NH and –OH groups in its two tautomeric forms has been synthesized and its excited state intramolecular proton transfer (ESIPT) reaction has been investigated by UV–vis, fluorescence, 1H NMR spectroscopy in combination with computational calculations. The experimental findings show that FP2HN selectively recognizes F−, AcO− and H2PO4− ions through the formation of –N(O)H⋯X hydrogen bonding (HB) complex. The binding constant obtained by non-linear fit predicts the binding order of F− > AcO− > H2PO4− > Cl−. The ESIPT process of FP2HN is inhibited either by the fluoride induced deprotonation of acidic proton of FP2HN or by the formation of a strong –N(O)H⋯X intermolecular hydrogen bonding complex. Further insights into the recognition mechanism of the receptor–anion complexes using ab initio calculations have been performed which support the experimental binding affinity order of F− > AcO− > H2PO4− > Cl−.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Study of basic photophysics of FP2HN using UV–vis, fluorescence, 1H NMR spectroscopy. ► ESIPT reaction and its inhibition by anions in FP2HN. ► Selective anions recognition by hydrogen bonding interaction and efficient deprotonation. ► Quantum chemical calculation.

Keywords
5-(4-Fluoro-phenyl)-2-hydroxy-nicotinonitrile; 5-(4-Fluoro-phenyl)-2-hydroxypyridine; Hydrogen bonding; Proton abstraction; Tetra-n-butylammonium; Hartree Fock
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Selective anion recognition by inhibition of excited state intramolecular proton transfer process via hydrogen bonding interaction and efficient deprotonation: Spectroscopic and theoretical investigation
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 232, 15 March 2012, Pages 64–72
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
Online Support
Any Questions? feel free to contact us