Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor properties

Tikhomirova, K.V.; Khoroshutin, A.V.; Anisimov, A.V.

Авторы: Tikhomirova K.V., Khoroshutin A.V., Anisimov A.V.
Журнал: Russian Journal of Organic Chemistry
Том: 50
Номер: 2
Год издания: 2014
Издательство: Maik Nauka/Interperiodica Publishing
Местоположение издательства: Russian Federation
Первая страница: 229
Последняя страница: 239
DOI: 10.1134/S1070428014020158
Аннотация: meso-Aryl-substituted (biscyclohexano)bis(ethoxycarbonyl)BODIPY [aryl = phenyl, 3,4-dimethoxyphenyl, and 2,3,5,6,8,9,11,12-octahydro-1,4,7,10,13-benzopentaoxacyclopentadecin-15-yl-(m-{benzo-15-crown-5}-yl)] were synthesized. The effect of alkaline-earth metals on the absorption and fluorescence spectra of these compounds was investigated. In all compounds along with the mechanism of the photoinduced electron transfer (PET), well-known for the crown-containing BODIPY-based sensors, one more response pattern is observed. The large excess of Ca2+ and Ba2+ ions in the system leads to the changes both in the UV-Vis and emission spectra. The complex formation results in the decrease of emission intensity and in its red shift. Besides, a new longwave absorption band appears in the UV-Vis spectrum of the BODIPY-metal ion complex. The formation constants of the complexes corresponding to this response pattern is about 100 times less than the formation constant of Ca2+-crown ether complex. H-1, C-13, B-11, and F-19 NMR spectra, the results of quantum-chemical calculations, and their comparison with the literature data of X-ray diffraction study suggest that the binding of Ca2+ and Ba2+ ions occurs in the cavity formed by the fluorine atoms and the carbonyl oxygen atoms of the ester groups.
Добавил в систему: Хорошутин Андрей Васильевич

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Diethyl (biscyclohexano)BODIPY dicarboxylates. Chelation of alkaline-earth metal ions and sensor propertiesстатья

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