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N‐Heterocyclic Carbene Boranes as Electron‐Donating and Electron‐Accepting Components of π‐Conjugated Systems
Author(s) -
Nagura Kazuhiko,
Saito Shohei,
Fröhlich Roland,
Glorius Frank,
Yamaguchi Shigehiro
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204050
Subject(s) - thiophene , borane , moiety , carbene , boranes , chemistry , conjugated system , photoisomerization , ring (chemistry) , electron , photochemistry , combinatorial chemistry , organic chemistry , polymer , isomerization , physics , boron , catalysis , quantum mechanics
Give and take : The introduction of NHC–borane moieties to thiophene‐based π skeletons endows a zwitterionic character, which makes the π system electron‐donating, while the NHC ring acts as an electron‐accepting moiety. The NHC–borane‐substituted thiophene underwent a clean photoisomerization with a drastic color change, however, the expanded bithiophene derivatives were inert to this photoreaction, showed low oxidation potentials, and formed a slipped π‐stacked array in the crystal.