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

• Authors: Oleksiy Grygorovych , Oleksiy Nevskii , Sofia Moskalenko , Vasyl Pivovarenko , Andrey Doroshenko
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

Dicyclopentano[b,e]pyridines; Electronic absorption spectra; Fluorescence spectra; Protolytic interactions; Wide range pH indicators; Photochemical E→Z isomerization

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2010
• Volume: 8
• Issue: 4
• Pages: 766-782

Dates

published

1 - 8 - 2010

online

17 - 6 - 2010

Contributors

author

Oleksiy Grygorovych

• Institute for Chemistry at Kharkov V.N. Karazin National University, Kharkov, 61077, Ukraine

author

Oleksiy Nevskii

• Institute for Chemistry at Kharkov V.N. Karazin National University, Kharkov, 61077, Ukraine

author

Sofia Moskalenko

• Institute for Chemistry at Kharkov V.N. Karazin National University, Kharkov, 61077, Ukraine

author

Vasyl Pivovarenko

• Department of Chemistry, Taras Shevchenko National University of Kyiv, Kyiv, 01033, Ukraine

author

Andrey Doroshenko

• Institute for Chemistry at Kharkov V.N. Karazin National University, Kharkov, 61077, Ukraine

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Identifiers

DOI

10.2478/s11532-010-0051-x