The Influence of the π-Conjugated Spacer on Photophysical Properties of Difluoroboranyls Derived from Amides Carrying a Donor Group

The Journal of Organic Chemistry
Anna Maria GrabarzB Ośmiałowski

Abstract

A series of difluoroboranyls derived from amides carrying a variable π-conjugated spacer between the electron-donating (D) and electron-accepting (A) groups was synthesized and characterized with (1)H, (11)B, (13)C, (15)N, and (19)F NMR, electronic absorption, fluorescence spectroscopies, and first-principle calculations. The D-to-A distance in the series varied from 1.5 to 4.5 Å, causing bathochromic shifts of both the absorption and fluorescence maxima by more than 120 and 213 nm, respectively. These trends are rationalized by quantum-mechanical calculations that allow for quantification of the charge-transfer distance. Theoretical calculations were also performed to determine the vibronic couplings and thus to reproduce the experimental band shapes.

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Citations

Oct 5, 2016·The Journal of Organic Chemistry·Denis FrathGilles Ulrich
Jan 10, 2017·The Journal of Organic Chemistry·Anna Maria GrabarzBorys Ośmiałowski
Jul 3, 2018·Organic & Biomolecular Chemistry·Kseniya I LugovikNataliya P Belskaya
Sep 14, 2019·The Journal of Physical Chemistry. a·Krzysztof DurkaSergiusz Luliński
Jan 10, 2018·The Journal of Organic Chemistry·Xiaokang LvErhong Hao
Jan 5, 2018·The Journal of Organic Chemistry·Mykhaylo A PotopnykJuozas Vidas Gražulevičius
Feb 6, 2017·Biomacromolecules·Caroline KerrCassandra L Fraser
Jul 7, 2020·The Journal of Physical Chemistry Letters·Borys OśmiałowskiDenis Jacquemin
Sep 4, 2018·The Journal of Organic Chemistry·Mykhaylo A PotopnykJuozas Vidas Gražulevičius
Jun 23, 2018·The Journal of Organic Chemistry·Beata JędrzejewskaBorys Ośmiałowski
Apr 10, 2020·The Journal of Organic Chemistry·Mykhaylo A PotopnykJuozas V Grazulevicius
Dec 6, 2021·Acta Crystallographica. Section C, Structural Chemistry·Borys OśmiałowskiLiliana Dobrzańska

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