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Preparation and Characterization of a π‐Conjugated Donor–Acceptor System Containing the Strongly Electron‐Accepting Tetraphenylborolyl Unit
Author(s) -
Meier Michael,
Ji Lei,
Nitsch Jörn,
Krummenacher Ivo,
Deißenberger Andrea,
Auerhammer Dominic,
Schäfer Marius,
Marder Todd B.,
Braunschweig Holger
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201805454
Subject(s) - carbazole , acceptor , cyclic voltammetry , electron donor , photochemistry , chemistry , electron acceptor , conjugated system , materials science , thiophene , electrochemistry , organic chemistry , polymer , electrode , catalysis , physics , condensed matter physics
A novel thiophene‐bridged donor–acceptor system was synthesized with a carbazole as donor and a borole as acceptor unit. The borole group was successfully installed via the tin–boron exchange reaction of 1,1‐dimethyl‐2,3,4,5‐tetraphenylstannole with 9‐(5‐(dibromoboryl)thiophen‐2‐yl)carbazole. The effect of the borole on the optoelectronic properties of the donor–acceptor system was explored by spectroscopic (UV/Vis and fluorescence spectroscopy), electrochemical (cyclic voltammetry) and theoretical (TD‐DFT) methods as well as by modifying its structure. The corresponding donor–acceptor compound bearing the widely employed dimesitylboryl acceptor group was also synthesized for comparison.