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Issue 8, 2010
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Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

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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.

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

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Publication details

The article was received on 02 Oct 2009 and first published on 07 Jun 2010


Article type: Tutorial Review
DOI: 10.1039/B904087K
Citation: Chem. Soc. Rev., 2010,39, 2879-2890
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    Synthetic approaches to aromatic belts: building up strain in macrocyclic polyarenes

    D. Eisenberg, R. Shenhar and M. Rabinovitz, Chem. Soc. Rev., 2010, 39, 2879
    DOI: 10.1039/B904087K

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