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Functionalization of Azapentabenzocorannulenes by Fivefold C−H Borylation and Cross‐Coupling Arylation: Application to Columnar Liquid‐Crystalline Materials
Author(s) -
Nagano Taro,
Nakamura Kimihiro,
Tokimaru Yuki,
Ito Shingo,
Miyajima Daigo,
Aida Takuzo,
Nozaki Kyoko
Publication year - 2018
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.201803676
Subject(s) - borylation , regioselectivity , surface modification , derivatization , coupling reaction , chemistry , conjugated system , iridium , template , combinatorial chemistry , materials science , catalysis , aryl , nanotechnology , organic chemistry , polymer , alkyl , high performance liquid chromatography
Herein, the one‐shot fivefold functionalization of azapentabenzocorannulenes by an iridium‐catalyzed fivefold C−H borylation reaction that exhibits excellent regioselectivity is reported. The borylated product can be used as a versatile synthetic intermediate for further derivatization via Suzuki–Miyaura cross‐coupling reactions. This fivefold borylation/arylation sequence was employed to synthesize liquid‐crystalline azapentabenzocorannulenes with five 3,4,5‐trialkoxyphenyl groups, which assemble into 1D hexagonal columnar structures over a wide temperature range. The present method expands the variety and utility of azapentabenzocorannulenes as promising π‐conjugated cores.