Issue 6, 2017

Chirality in curved polyaromatic systems

Abstract

Carbon allotropes constituted of sp2-hybridised carbon atoms display a variety of properties that arise from their delocalised π-conjugated electronic structure. Apart from carbon's planar allotropic form graphene, bent or curved structures, such as carbon nanotubes or fullerenes, respectively, have been discovered. In this Tutorial Review, we analyse and conceptually categorise chiral synthetic molecular fragments of non-planar sp2-carbon allotropes, including hypothetical forms of carbon that have been proposed to exist as stable entities. Two types of molecular systems composed of equally or differently sized rings are examined: bent with zero Gaussian curvature and curved with positive or negative Gaussian curvature. To affirm that a system is chiral, two conditions must be fulfilled: (1) both reflective symmetry elements, an inversion centre and a mirror plane, must be absent and (2) the system must be stereochemically rigid. It is therefore crucial to not only consider the symmetry of a given system as if it was a rigid object but also its structural dynamics. These principles serve as guidelines for the design of molecular fragments that encode and transcribe chirality into larger systems.

Graphical abstract: Chirality in curved polyaromatic systems

  • This article is part of the themed collection: Primer

Supplementary files

Article information

Article type
Tutorial Review
Submitted
18 aug 2016
First published
22 feb 2017

Chem. Soc. Rev., 2017,46, 1643-1660

Author version available

Chirality in curved polyaromatic systems

M. Rickhaus, M. Mayor and M. Juríček, Chem. Soc. Rev., 2017, 46, 1643 DOI: 10.1039/C6CS00623J

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