X-shaped thiadiazole-containing double [7]heterohelicene with strong chiroptical response and π-stacked homochiral assembly

Juan Hong; Xuxian Xiao; Haoliang Liu; Lin Fu; Xin-Chang Wang; Long Zhou; Xiao-Ye Wang; Zijie Qiu; Xiao-Yu Cao; Akimitsu Narita; Klaus Müllen; Yunbin Hu

doi:10.1039/D1CC01631H

X-shaped thiadiazole-containing double [7]heterohelicene with strong chiroptical response and π-stacked homochiral assembly†

Juan Hong,‡^a Xuxian Xiao,‡^a Haoliang Liu,^b Lin Fu,^c Xin-Chang Wang,^b Long Zhou,^a Xiao-Ye Wang,

^c Zijie Qiu,^d Xiao-Yu Cao,

^b Akimitsu Narita,

^d Klaus Müllen^d and Yunbin Hu

*^a

Author affiliations

* Corresponding authors

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

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

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

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

Abstract

An X-shaped double [7]heterohelicene 1 bearing four thiadiazole units is synthesized by regioselective cyclodehydrogenation. Enantiopure 1 exhibits excellent chiroptical properties with an impressive absorption dissymmetry factor of up to 0.027, as well as a compact π-stacked homochiral assembly which is unprecedented in the realm of double helicenes.

Chemical Communications

X-shaped thiadiazole-containing double [7]heterohelicene with strong chiroptical response and π-stacked homochiral assembly†

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X-shaped thiadiazole-containing double [7]heterohelicene with strong chiroptical response and π-stacked homochiral assembly

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