Double [4]Helicene-like Naphthobisbenzothiophene Diimides and Their Thienyl-S,S-dioxidized Derivatives with Attractive Solid-State Fluorescence and High Electron Affinity

Xingyu Yi; Junxiang Gao; Hanwen Qin; Liping Zheng; Weixuan Zeng; Huajie Chen

doi:10.1021/acs.orglett.3c00001

Double [4]Helicene-like Naphthobisbenzothiophene Diimides and Their Thienyl-S,S-dioxidized Derivatives with Attractive Solid-State Fluorescence and High Electron Affinity

Org Lett. 2023 Feb 17;25(6):972-976. doi: 10.1021/acs.orglett.3c00001. Epub 2023 Feb 2.

Authors

Xingyu Yi¹, Junxiang Gao¹, Hanwen Qin¹, Liping Zheng¹, Weixuan Zeng², Huajie Chen¹

Affiliations

¹ Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, China.
² Department of Chemistry, University of Cambridge, Cambridge, CB2 1EW, U.K.

PMID: 36732283
DOI: 10.1021/acs.orglett.3c00001

Abstract

A series of double [4]helicene-like naphthobisbenzothiophene diimides and their thienyl-S,S-dioxidized derivatives are synthesized via MoCl₅-catalyzed cyclization and m-CPBA-mediated oxidation reactions. The functional five-membered ring diimides show a helicene-like geometry, strong solid-state fluorescence, and deep LUMO of -4.37 eV.