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

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• 作者：Beata Jędrzejewska ; Anna Zakrzewska ; Grzegorz Mlostoń ; Šimon Budzák ; Karina Mroczyńska ; Anna M. Grabarz ; Małgorzata A. Kaczorowska ; Denis Jacquemin ; Borys Ośmiałowski
• 刊名：Journal of Physical Chemistry A
• 出版年：2016
• 出版时间：June 23, 2016
• 年：2016
• 卷：120
• 期：24
• 页码：4116-4123
• 全文大小：416K
• 年卷期：0
• ISSN：1520-5215

文摘

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.