Saiyasombat W.Eiamprasert U.Chantarojsiri T.Chainok K.Kiatisevi S.Mahidol University2023-06-182023-06-182022-10-01Dyes and Pigments Vol.206 (2022)01437208https://repository.li.mahidol.ac.th/handle/20.500.14594/84048A novel bis-BODIPY-based colorimetric and fluorescent sensor (BODIPY-NN) for F− and CN− recognition with high selectivity and high sensitivity is reported. The designed sensor, BODIPY-NN, was synthesized by a one-step click reaction of azido-BODIPY with N,N′-dipropargylbenzene-1,2-diamine. The BODIPY-NN sensor displays a marked color change from pink to colorless and a remarkable turn-off fluorescence behavior exclusively toward F− and CN− ions. Analysis of 1H, 13C, 19F, 11B NMR and mass spectra, together with theoretical calculations, provides insight into the mechanism of anion binding to BODIPY-NN. The sensing mechanism was found to be unconventional deprotonation at pseudo-benzylic carbons attached to BODIPY cores in the presence of F− and CN− ions, to form the less highly conjugated BODIPY moieties, thereby displaying fluorescence quenching. Addition of water in the BODIPY-NN + F− system regenerates the sensor with restoration of its spectroscopic properties. In contrast, the CN− ions permanently disrupt the BODIPY moieties by nucleophilic displacement at the central boron atoms, which is irreversible upon addition of water. The detection limits for F− and CN− in THF are 83 and 72 nM, respectively. In particular, BODIPY-NN embedded in cetyltrimethylammonium micelles can be used as colorimetric detection of CN− ions in aqueous media.Chemical EngineeringArticleSCOPUS10.1016/j.dyepig.2022.1106432-s2.0-8513582098818733743