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Synthesis and Properties of Thiophene‐Fused Benzocarborane
Author(s) -
Morisaki Yasuhiro,
Tominaga Masato,
Chujo Yoshiki
Publication year - 2012
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.201201513
Subject(s) - moiety , thiophene , ring (chemistry) , conjugated system , carborane , aromaticity , homo/lumo , crystal structure , coplanarity , polar effect , crystallography , chemistry , unit (ring theory) , stereochemistry , materials science , polymer , molecule , photochemistry , organic chemistry , geometry , mathematics , mathematics education
The o ‐carborane‐based π‐conjugated compound, benzocarborano‐ [2,1‐ b :3,4‐ b ′]dithiophene was synthesized. Its crystal structure revealed high coplanarity for the two thiophene rings of the 2,2′‐bithiophene skeleton, which is fixed in the cisoid structure by the o ‐carborane unit. Theoretical calculations indicated non‐aromaticity for its center C 6 ring moiety as well as decreased HOMO and LUMO levels. The o ‐carborane moiety provides an electron‐withdrawing character to the 2,2′‐bithiophene unit through an inductive effect.