Photoswitchable dihetarylethene chemosensors for the selective 'naked-eye' detection of fluoride anions. Issue 46 (18th November 2015)

• Record Type: Journal Article
• Authors: Dubonosov, Alexander D.; Bren, Vladimir A.; Minkin, Vladimir I.; Shepelenko, Evgenii N.; Tikhomirova, Karina S.; Starikov, Andrey G.; Revinskii, Yurii V.
• Is Part Of: Tetrahedron. Volume 71:Issue 46(2015)
• Page Start: 8817
• Page End: 8822
• Publication Date: 2015-11-18
• Subjects: Dihetarylethene -- Photochromism -- Chemosensor -- Chemodosimeter -- Fluoride anion; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2015.09.030
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Novel photochromic thiazole-bridged dihetarylethenes with coumarinyl and thiophenyl substituents were synthesized. Their interaction either in ring-opened or in cyclic forms with fluoride, cyanide or acetate anions leads to drastic visibly detected changes in the electronic absorption spectra (yellow-to-violet color change), whereas other anions (Cl −, Br −, I −, SCN −, NO3 −, HSO4 − and H2 PO4 − ) do not induce any considerable colorimetric changes. Only in the case of fluoride ions, this effect is accompanied by very fast consecutive bleaching of solutions (violet-to-yellowish color change) owing to irreversible deprotonation of the NH moiety. This mechanism is supported by the results of the DFT calculations. Graphical abstract: