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BY-NC-ND 3.0 license Open Access Published by De Gruyter Open Access June 17, 2010

Protolytic properties of the structurally rigid analogs of 2,6-distyrylpyridine. Widening the pH sensitivity range by the photochemical E→Z isomerisation and introduction of substituents capable to protolytic interactions

Oleksiy Grygorovych, Oleksiy Nevskii, Sofia Moskalenko, Vasyl Pivovarenko and Andrey Doroshenko
From the journal Open Chemistry

Abstract

Protolytic interactions in the series of prospective fluorescent ratiometric wide-range pH indicators — structurally rigid analogs of 2,6-distyrylpyridine — (3E,5E)-3,5-dibenzylidene-8-phenyl-1,2,3,5,6,7-hexahydrodicyclopentano[b,e]pyridine — were investigated. The pyridine nitrogen atom basicity in these compounds is significantly lower in comparison with that of unsubstituted heterocycle and 2,6-distyrylpyridine. The photochemical E→Z photoisomerization and the side benzene rings substituents influence on the acid-base equilibria were studied. The complex multi-stage mechanism of the acid-base interactions of the polysubstituted compounds was elucidated. The most significant spectral effects were typical to the N,N-dialkylamino substituted compounds of the investigated series. The widest pH sensitivity interval covering nearly the full range of 0–14 units was demonstrated for compounds with both proton donor and proton acceptor substituents.

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Published Online: 2010-6-17
Published in Print: 2010-8-1

© 2010 Versita Warsaw

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