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 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.
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology , Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
Beata
B
Jędrzejewska
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology , Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
Anna
A
Zakrzewska
Faculty of Chemistry, University of Łódź , Tamka 12, PL-91403 Łódź, Poland.
Grzegorz
G
Mlostoń
Faculty of Natural Sciences, Matej Bel University , Tajovského 40, 974 01 Banská Bystrica, Slovakia.|Laboratoire CEISAM, UMR CNRS 6230, Universite de Nantes , 2 Rue de la Houssinière, BP92208, 44322 Cedex 3 Nantes, France.
Šimon
Š
Budzák
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology , Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
Karina
K
Mroczyńska
Faculty of Chemistry, Wrocław University of Technology , Wyb. Wyspiańskiego 27, PL-50370 Wrocław, Poland.
Anna M
AM
Grabarz
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology , Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
Małgorzata A
MA
Kaczorowska
Laboratoire CEISAM, UMR CNRS 6230, Universite de Nantes , 2 Rue de la Houssinière, BP92208, 44322 Cedex 3 Nantes, France.|Institut Universitaire de France , 1, Rue Descartes, 75005 Paris, France.
Denis
D
Jacquemin
Faculty of Chemical Technology and Engineering, UTP University of Science and Technology , Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
Borys
B
Ośmiałowski