Efficient Synthesis of 1, 4‐Bis‐heteroatom‐substituted Tetraselanylbenzenes via 1, 4‐Dilithiation of Hexaselanylbenzene and Investigation on Their Electronic Properties. Issue 9 (16th March 2017)

• Record Type: Journal Article
• Authors: Fujita, Masahiro; Furukawa, Shunsuke; Saito, Masaichi
• Is Part Of: Chemistry, an Asian journal. Volume 12:Issue 9(2017)
• Page Start: 954
• Page End: 957
• Publication Date: 2017-03-16
• Subjects: cyclic voltammetry -- heteroatom-substituted benzenes -- 77Se NMR spectroscopy -- selanylbenzenes -- transmetalation; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/asia.201700164
• Languages: English
• ISSNs: 1861-4728

Abstract

Abstract: We successfully synthesized mono‐ and bis‐substituted polyselanylbenzenes3 and5 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 benzenes5, the extent of the interactions in the circular orbitals with σ‐symmetry affected the stability of the cationic species of5 . 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. Abstract : Tuning σ‐type orbital interactions : Bis‐heteroatom‐substituted benzenes5 bearing various heteroatom functionalities were synthesized via the dilithiation of hexaselanylbenzene1 . The 77 Se NMR, cyclic voltammetry and theoretical studies revealed that the electronic properties of5 change depending on the heteroatom functionalities.