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

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.

SUBMITTER: Su F

PROVIDER: S-EPMC8148024 | biostudies-literature | 2019 Dec

REPOSITORIES: biostudies-literature

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

Su Feng F Chen Shuqi S Mo Xiaogang X Wu Kongchuan K Wu Jiajun J Lin Weidong W Lin Zhiwei Z Lin Jianbin J Zhang Hui-Jun HJ Wen Ting-Bin TB

Chemical science 20191220 6

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 thie ...[more]

PMID: 34084379

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