Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Feng Su; Shuqi Chen; Xiaogang Mo; Kongchuan Wu; Jiajun Wu; Weidong Lin; Zhiwei Lin; Jianbin Lin; Hui-Jun Zhang; Ting-Bin Wen

doi:10.1039/c9sc05332h

Trisulfur radical anion-triggered stitching thienannulation: rapid access to largely π-extended thienoacenes

Chem Sci. 2019 Dec 20;11(6):1503-1509. doi: 10.1039/c9sc05332h.

Authors

Feng Su¹, Shuqi Chen¹, Xiaogang Mo¹, Kongchuan Wu¹, Jiajun Wu¹, Weidong Lin¹, Zhiwei Lin¹, Jianbin Lin^{1

2}, Hui-Jun Zhang¹, Ting-Bin Wen¹

Affiliations

¹ Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 Fujian P. R. China [email protected].
² MOE Key Laboratory of Spectrochemical Analysis and Instrumentation, Xiamen University Xiamen 361005 P. R. China.

Abstract

Largely π-extended rylene diimide-fused thienoacenes, a new family of fully fused electron donor-acceptor (D-A) molecules, have been readily synthesized by a novel trisulfur radical anion (S₃˙^-)-triggered stitching thienannulation strategy. The ladder-type fused thiophene cores are constructed in a stitching manner through multiple carbon-sulfur bond formation between acetylenic rylene dyes and S₃˙^-. A detailed mechanistic study of these stitching thienannulations unveiled the multiple reactivities of S₃˙^-. Physical properties of the newly formed D-A, A-D-A, and D-A-D type thienoacenes have also been investigated, which revealed their precisely controllable electronic properties.