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Synlett 2020; 31(20): 1957-1961
DOI: 10.1055/s-0040-1706411
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© Georg Thieme Verlag Stuttgart · New York

Embedding Heteroatoms and Adjacent Pentagons in Concave Molecules

Gang Zhang  ∗
This work was supported by the Jiangsu Specially Appointed Professor Plan.
Further Information

Publication History

Received: 29 June 2020

Accepted after revision: 11 July 2020

Publication Date:
10 August 2020 (online)

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Abstract

Bowl-shaped molecules, which can be viewed as fragments of fullerenes, have been extensively studied owing to their interesting fundamental properties derived from their unique geometry, and the possibilities for their further functionalization, with potential applications in the field of materials science. Most of the reported concave compounds are based on corannulene or sumanene, the simplest representative fullerene subunits possessing isolated pentagons. Syntheses of concave molecules bearing adjacent pentagons have rarely been reported. Inspired by the structure of N-heterotriangulene, the construction of bowl-shaped compounds containing two fused pentagons and a central nitrogen atom is discussed. Further surface extension of such concave molecules can result in the formation of boat-shaped compounds containing embedded double isolated nitrogen atoms.

Key words

acridones - aromaticity - buckybowls - conjugation - heterotriangulene - polycyclic aromatic hydrocarbons
 

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