N-heterocyclic carbene boranes as electron-donating and electron-accepting components of π-conjugated systems.
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.
Department of Chemistry, Graduate School of Science, Nagoya University, Furo, Chikusa, Nagoya 464-8602, Japan.
Kazuhiko
K
Nagura
Shohei
S
Saito
Roland
R
Fröhlich
Frank
F
Glorius
Shigehiro
S
Yamaguchi
D001880:Boranes / Q000138:chemical synthesis / Q000737:chemistry*; D004563:Electrochemistry; D004583:Electrons; D006571:Heterocyclic Compounds / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D011789:Quantum Theory
D001880:Boranes; D006571:Heterocyclic Compounds; C030011:carbene; D008697:Methane