Furan-containing double tetraoxa[7]helicene and its radical cation

Hao Chang; Haoliang Liu; Evgenia Dmitrieva; Qiang Chen; Ji Ma; Piao He; Pengcai Liu; Alexey A. Popov; Xiao-Yu Cao; Xiao-Ye Wang; Yingping Zou; Akimitsu Narita; Klaus Müllen; Hongjian Peng; Yunbin Hu

doi:10.1039/D0CC06970A

Furan-containing double tetraoxa[7]helicene and its radical cation†

Hao Chang,^a Haoliang Liu,^b Evgenia Dmitrieva,^c Qiang Chen,^d Ji Ma,

^e Piao He,

^a Pengcai Liu,^f Alexey A. Popov,

^g Xiao-Yu Cao,

^b Xiao-Ye Wang,

^f Yingping Zou,

^a Akimitsu Narita,^g Klaus Müllen,

^g Hongjian Peng*^a and Yunbin Hu

*^a

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* Corresponding authors

^a College of Chemistry and Chemical Engineering, Central South University, Changsha, Hunan 410083, P. R. China
E-mail: penghongjian@csu.edu.cn, huyunbin@csu.edu.cn

^b Department of Chemistry and Chemical Engineering, Xiamen University, 361005 Xiamen, China

^c Center of Spectroelectrochemistry, Leibniz Institute for Solid State and Materials Research, Helmholtzstrasse 20, 01069 Dresden, Germany

^d Max Planck Institute for Polymer Research, Ackermannweg 10, 55128 Mainz, Germany

^e Centre for Advancing Electronics Dresden (cfaed), Faculty of Chemistry and Food Chemistry, Technische Universität Dresden, 01062 Dresden, Germany

^f State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Weijin Road 94, Tianjin, China

^g Organic and Carbon Nanomaterials Unit, Okinawa Institute of Science and Technology Graduate University, 1919-1 Tancha, Onna-son, Kunigami-gun, Okinawa 904-0495, Japan

Abstract

An unprecedented furan-based double oxa[7]helicene 1 was achieved, featuring a stable twisted conformation with π-overlap at both helical ends. The excellent conformational stability allowed for optical resolution of 1, which provided a pair of enantiomers exhibiting pronounced mirror-imaged circular dichroism and circularly polarized luminescence activity. The radical cation of 1 was obtained by chemical oxidation as evidenced by UV-Vis-NIR absorption, electron paramagnetic resonance spectroscopy and in situ spectroelectrochemistry. The present work is the starting point for the investigation of open-shell oxahelicenes.

Chemical Communications

Furan-containing double tetraoxa[7]helicene and its radical cation†

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Furan-containing double tetraoxa[7]helicene and its radical cation

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