Fluoride-responsive gelator and colorimetric sensor based on simple and easy-to-prepare cyano-substituted amide?

Organic & Biomolecular Chemistry Pub Date: 2012-07-13 DOI: 10.1039/C2OB26016F

Abstract

A new and easy-to-prepare gelator based on cyano-substituted amide (BPNIA) was designed and synthesized. BPNIA could form thermoreversible gel in DMSO–H2O (v/v, 9?:?1) and ultrasound-stimulated gel in DMSO. FT-IR, UV–vis and XRD spectra indicated that the gelator molecules self-assemble into a fibrous network resulting from the cooperation of intermolecular hydrogen bonding, π–π stacking and cyano interactions. BPNIA can act as a highly selective colorimetric sensor for fluoride in DMSO, overcoming the interference of H2PO4?, AcO? and other halide anions. The deprotonation of the NH groups is responsible for the dramatic color change from colorless to yellow. Interestingly, the organogel of BPNIA could allow a two channel fluoride response by proton controlled reversible sol–gel transition and color changes.

Graphical abstract: Fluoride-responsive gelator and colorimetric sensor based on simple and easy-to-prepare cyano-substituted amide
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