Synthesis and Photophysical Properties of Novel Donor–Acceptor N‑(Pyridin-2-yl)-Substituted Benzo(thio)amides and Their Difluoroboranyl Derivatives

The unprecedented N-pyridin-2-yl substituted benzo­(thio)­amides were prepared and subsequently converted into the cyclic difluoroboranyl (BF2) derivatives. Mass spectrometry, multinuclear NMR, IR, and elemental analysis confirmed the structure of these compounds. UV/vis and fluorescence spectroscop...

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Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2016-06, Vol.120 (24), p.4116-4123
Main Authors: Jędrzejewska, Beata, Zakrzewska, Anna, Mlostoń, Grzegorz, Budzák, Šimon, Mroczyńska, Karina, Grabarz, Anna M, Kaczorowska, Małgorzata A, Jacquemin, Denis, Ośmiałowski, Borys
Format: Article
Language:English
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Chemical Sciences
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Summary:The unprecedented N-pyridin-2-yl substituted benzo­(thio)­amides were prepared and subsequently converted into the cyclic difluoroboranyl (BF2) derivatives. Mass spectrometry, multinuclear NMR, IR, and elemental analysis confirmed the structure of these compounds. UV/vis and fluorescence spectroscopy as well as first-principle calculations were used to study their properties. For the first time, the influence of both the O/S replacement and presence/absence of the BF2 moiety on the photophysical properties of compounds exhibiting charge transfer properties were examined experimentally and theoretically. We show that the sulfur-containing compound has a much smaller emission quantum yield than its oxygen counterpart. The fluorescence quantum yield is much higher upon formation of the difluoroboranyl complex.
ISSN:1089-5639
1520-5215
DOI:10.1021/acs.jpca.6b04004