Efficient Synthesis of 1,4-Bis-heteroatom-substituted Tetraselanylbenzenes via 1,4-Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties

Masahiro Fujita; Shunsuke Furukawa; Masaichi Saito

doi:10.1002/asia.201700164

Efficient Synthesis of 1,4-Bis-heteroatom-substituted Tetraselanylbenzenes via 1,4-Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties

Chem Asian J. 2017 May 4;12(9):954-957. doi: 10.1002/asia.201700164. Epub 2017 Mar 16.

Authors

Masahiro Fujita¹, Shunsuke Furukawa¹, Masaichi Saito¹

Affiliation

¹ Department of Chemistry, Graduate School of Science and Engineering, Saitama University, Shimo-okubo, Sakura-ku, Saitama, 338-8570, Japan.

PMID: 28206706
DOI: 10.1002/asia.201700164

Abstract

We successfully synthesized mono- and bis-substituted polyselanylbenzenes 3 and 5 via mono- and dilithiation of hexakis(phenylselanyl)benzene (1), respectively. Introduction of various heteroatom functionalities into hexaselanylbenzene changed the electronic properties dependent on the σ-symmetric circular orbitals that were formed by the interactions between neighboring heteroatoms. In the cyclic voltammetry and theoretical studies on bis-heteroatom-substituted benzenes 5, the extent of the interactions in the circular orbitals with σ-symmetry affected the stability of the cationic species of 5. This study would give insight into the molecular design for new σ-delocalized systems and inspire the development of tuning electronic properties of benzene derivatives by σ-type orbital interactions derived from heteroatom functionalities.

Keywords: 77Se NMR spectroscopy; cyclic voltammetry; heteroatom-substituted benzenes; selanylbenzenes; transmetalation.