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. 2010 Aug;39(8):2879-90.
doi: 10.1039/b904087k. Epub 2010 Jun 7.

Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

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Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

David Eisenberg et al. Chem Soc Rev. 2010 Aug.

Abstract

This tutorial review discusses synthetic strategies towards aromatic belts, defined here as double-stranded conjugated macrocycles, such as [n]cyclacenes, [n]cyclophenacenes, Schlüter belt, and Vögtle belt. Their appeal stems, firstly, from the unique nature of their conjugation, having p orbitals oriented radially rather than perpendicular to the plane of the macrocycle. Secondly, as aromatic belts are model compounds of carbon nanotubes of different chiralities, a synthetic strategy towards the buildup of structural strain in these compounds could finally open a route towards rational chemical synthesis of carbon nanotubes. The elusiveness of these compounds has stimulated fascinating and ingenious synthetic strategies over the last decades. The various strategies are classified here by their approach to the buildup of structural strain, which is the main obstacle in the preparation of these curved polyarenes.

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