Issue 18, 2022

Corannulene-based acenes

Abstract

Synthesis of diacenes still represents a considerable challenge due to their poor stability and low solubility. In this work, we have designed and synthesized two novel corannulene-based pentacenes, CORA-monPA and CORA-bisPA. X-ray crystallographic analysis revealed their unique geometry and slip-stack columnar structure. Furthermore, the absorption and emission spectra in combination with DFT calculations were used to investigate the photophysical properties and (anti)aromaticity of CORA-monPA and CORA-bisPA. Importantly, the X-ray crystallographic analysis and 1H NMR investigations revealed that CORA-monPA underwent the Diels–Alder reaction with C60 to form the fullerene adduct CORA-monPA-C60, which is packed as two comma-shaped swirl-like structures in the solid phase.

Graphical abstract: Corannulene-based acenes

Supplementary files

Article information

Article type
Research Article
Submitted
08 Jul 2022
Accepted
01 Aug 2022
First published
04 Aug 2022

Org. Chem. Front., 2022,9, 4981-4989

Corannulene-based acenes

Q. Xu, C. Wang, X. Chen, Y. Wang, Z. Shen and H. Jiang, Org. Chem. Front., 2022, 9, 4981 DOI: 10.1039/D2QO01096H

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