A Nanoboat with Fused Concave N-Heterotriangulene

Angewandte Chemie
Gang Zhang, Leyong Zhou

Abstract

The surface extension of all-carbon based bowl-shaped molecules, such as corannulene, sumanene, to synthesize even larger buckybowls has been widely studied, leaving other concave compounds with heteroatoms less considered. Herein we present a highly curved molecule synthesized via the stepwise cyclization of fjords of a bisacridone derivative. Crystallographic analysis unambiguously confirmed a boat-shaped structure with deformed bottom benzene ring. Theoretical calculation unravels an inversion process with an S-shaped transition structure rather than a planar one. The enlarged boat demonstrates interesting properties, such as red shifts in absorption and emission spectra, enhanced emission intensity, a convergent molecular orbital energy levels, in comparison to the related concave N-heterotriangulene.

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Citations

Jun 17, 2020·Chemistry : a European Journal·Michael MastalerzFrank Rominger
Nov 17, 2020·Organic & Biomolecular Chemistry·Wenbo Wang, Xiangfeng Shao
Dec 8, 2020·The Journal of Organic Chemistry·Guanxing Zhu, Gang Zhang

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