o-Carborane-based biphenyl and p-terphenyl derivatives

Yasuhiro Morisaki; Masato Tominaga; Takuya Ochiai; Yoshiki Chujo

doi:10.1002/asia.201400067

o-Carborane-based biphenyl and p-terphenyl derivatives

Chem Asian J. 2014 May;9(5):1247-51. doi: 10.1002/asia.201400067. Epub 2014 Mar 3.

Authors

Yasuhiro Morisaki¹, Masato Tominaga, Takuya Ochiai, Yoshiki Chujo

Affiliation

¹ Department of Polymer Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510 (Japan), Fax: (+81) 75-383-2607. ymo@chujo.synchem.kyoto-u.ac.jp.

PMID: 24591100
DOI: 10.1002/asia.201400067

Abstract

The synthesis and properties of biphenyl- and p-terphenyl-fused o-carboranes are described. Aryl rings in the biphenyl and p-terphenyl skeletons are highly coplanar because of the presence of the o-carborane unit. o-Carborane exhibits an electron-withdrawing character via the inductive effect, resulting in a decrease in both the HOMO and LUMO levels of oligophenyls without causing electronic perturbation.

Keywords: benzocarborane; biphenyl; carboranes; electron-deficient compounds; p-terphenyl.