Bis-BODIPY-based fluoride and cyanide sensor mediated by unconventional deprotonation of C−H proton
1
Issued Date
2022-10-01
Resource Type
ISSN
01437208
eISSN
18733743
Scopus ID
2-s2.0-85135820988
Journal Title
Dyes and Pigments
Volume
206
Rights Holder(s)
SCOPUS
Bibliographic Citation
Dyes and Pigments Vol.206 (2022)
Suggested Citation
Saiyasombat W., Eiamprasert U., Chantarojsiri T., Chainok K., Kiatisevi S. Bis-BODIPY-based fluoride and cyanide sensor mediated by unconventional deprotonation of C−H proton. Dyes and Pigments Vol.206 (2022). doi:10.1016/j.dyepig.2022.110643 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/84048
Title
Bis-BODIPY-based fluoride and cyanide sensor mediated by unconventional deprotonation of C−H proton
Other Contributor(s)
Abstract
A 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.