Tetrathio and Tetraseleno[8]circulenes: Synthesis, Structures, and Properties

• Published in: Chemistry, an Asian journal Vol. 10; no. 4; pp. 969 - 975
• Main Authors: Xiong, Xiaodong, Deng, Chun-Lin, Minaev, Boris F., Baryshnikov, Gleb V., Peng, Xiao-Shui, Wong, Henry N. C.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.04.2015; WILEY‐VCH Verlag; Wiley Subscription Services, Inc
• Subjects: antiaromaticity; Chemistry; circulene; density functional theory calculation; electrochemistry; photophysics; antiaromaticity; photophysics; electrochemistry; circulene; density functional theory calculation
• ISSN: 1861-4728; 1861-471X
• DOI: 10.1002/asia.201403028

Novel sulfur and selenium‐bridged [8]circulenes were prepared from octabromotetraphenylene. Structures of these compounds were unambiguously confirmed by X‐ray crystallographic analyses. Photophysical and electrochemical investigations of these [8]circulenes suggest their potential applications as electronic materials. The antiaromatic nature of tetrathio[8]circulene and tetraselenium[8]circulene was studied by computational methods, and the NICS computational results reveal that the central eight‐membered ring has highly antiaromatic character. Quite a character: Novel sulfur and selenium‐bridged [8]circulenes were prepared from octabromotetraphenylene. Computational results show that the central eight‐membered rings in these [8]circulenes have a remarkably high antiaromatic character.