Premium
Efficient Synthesis of 1,4‐Bis‐heteroatom‐substituted Tetraselanylbenzenes via 1,4‐Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties
Author(s) -
Fujita Masahiro,
Furukawa Shunsuke,
Saito Masaichi
Publication year - 2017
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201700164
Subject(s) - heteroatom , delocalized electron , chemistry , atomic orbital , computational chemistry , benzene , cyclic voltammetry , molecular orbital , electronic structure , aromaticity , crystallography , ring (chemistry) , electrochemistry , molecule , organic chemistry , physics , quantum mechanics , electron , electrode
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.