Mechanisms of photoinduced protolytic interactions of 2,5-diphenyloxazoleortho-hydroxy derivatives in media of various acidities

A. D. Doroshenko; E. A. Posokhov

doi:10.1007/bf02761836

Mechanisms of photoinduced protolytic interactions of 2,5-diphenyloxazoleortho-hydroxy derivatives in media of various acidities

High Energy Chemistry ◽

10.1007/bf02761836 ◽

2000 ◽

Vol 34 (2) ◽

pp. 93-100 ◽

Cited By ~ 3

Author(s):

A. D. Doroshenko ◽

E. A. Posokhov

Keyword(s):

Protolytic Interactions

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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

Open Chemistry ◽

10.2478/s11532-010-0051-x ◽

2010 ◽

Vol 8 (4) ◽

pp. 766-782

Author(s):

Oleksiy Grygorovych ◽

Oleksiy Nevskii ◽

Sofia Moskalenko ◽

Vasyl Pivovarenko ◽

Andrey Doroshenko

Keyword(s):

Full Range ◽

Proton Donor ◽

Ph Sensitivity ◽

Proton Acceptor ◽

Acid Base ◽

Multi Stage ◽

Protolytic Interactions ◽

Pyridine Nitrogen ◽

Sensitivity Range ◽

Wide Range

AbstractProtolytic 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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