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Monoazadichalcogenasumanenes: Synthesis, Structures, and Ring Reconstruction via Atom Transfer under Acidic Conditions.

Authors :
Shang, Jihai
Wang, Renjie
Yuan, Chengshan
Liu, Zitong
Zhang, Hao‐Li
Shao, Xiangfeng
Source :
Angewandte Chemie; 5/23/2022, Vol. 134 Issue 22, p1-10, 10p
Publication Year :
2022

Abstract

Buckybowls have unique properties that can be tailored by embedding main‐group elements into their π‐scaffolds. Herein, a synthetic approach is developed for producing monoazadichalcogenasumanenes (4 a/4 b, 6 a/6 b, 7 a/7 b) derived from sumanene by replacing its three benzylic carbons with one nitrogen and two chalcogen atoms (S for 4 a/4 b, Se for 6 a/6 b, Te for 7 a/7 b). Monoazadichalcogenasumanenes are deeper π‐bowls than trichalcogensumanenes as the C−N bond is much shorter than C−X (X=S, Se, Te). The bowl‐depth of 4 b (0.95 Å) is greater than that of corannulene (0.85 Å). The nitrogen atom donates electron density to the entire π‐system that makes monoazadichalcogenasumanenes electron‐rich. They undergo ring reconstruction of chalcogenophene ring via transferring a chalcogen atom from one molecule to another under acidic conditions. The nitrogen and chalcogen atoms play crucial role on this reaction. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
00448249
Volume :
134
Issue :
22
Database :
Complementary Index
Journal :
Angewandte Chemie
Publication Type :
Academic Journal
Accession number :
156901810
Full Text :
https://doi.org/10.1002/ange.202117504