Synthesis, Structures and Properties of Trioxa[9]circulene and Diepoxycyclononatrinaphthalene

Author:

Yang Daiyue12,Cheung Ka Man3,Gong Qi3,Zhang Li3,Qiao Lulin12,Chen Xiao3,Huang Zhifeng3,Miao Qian32ORCID

Affiliation:

1. State Key Laboratory of Antiviral Drugs Pingyuan Laboratory School of Chemistry and Chemical Engineering Henan Normal University 453007 Xinxiang Henan China

2. Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis Shanghai Institute of Organic Chemistry Chinese Academy of Sciences 230032 Shanghai China

3. Department of Chemistry The Chinese University of Hong Kong Shatin, New Territories Hong Kong China

Abstract

AbstractThis article presents trioxa[9]circulene (3) as a novel member of hetero[n]circulenes. Its synthesis began with the synthesis of dimethoxydioxa[8]helicene (5) and used dimethoxydiepoxycyclononatrinaphthalene (4) as a key intermediate, despite the condensation reaction predominantly yielding a 1,4‐addition byproduct. The structures and properties of 35 were extensively investigated using experimental and computational methods. Analysis of the crystal structures reveal elongation of the internal C−C bonds in the nine‐membered ring of 3 compared to 4 and 5. Computational studies demonstrate the remarkable flexibility of trioxa[9]circulene's saddle‐shaped polycyclic framework, while the other two compounds are rigid with large racemization barriers. Optically pure forms of 4 and 5 exhibit absorption and luminescence dissymmetry factors on the order of 10−2, with smaller values observed for compound 4. In the crystal structures, molecules of 3 stack to form columns with remarkable π–π overlap, and the π–π interactions of 4 exhibit short intermolecular C‐to‐C contacts. Consequently, the solution‐processed film of 4 functioned as a p‐type organic semiconductor in field effect transistors.

Funder

Chinese University of Hong Kong

Publisher

Wiley

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