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芳香带的合成方法:大环多芳烃中环应变的构建。

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

机构信息

The Institute of Chemistry and the Lise Meitner-Minerva Center for Computational Quantum Chemistry, The Hebrew University of Jerusalem, Edmond J. Safra Campus, Givat Ram, Jerusalem, 91904, Israel.

出版信息

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

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.

摘要

本教程综述讨论了芳香带的合成策略,这里将其定义为双链共轭大环,例如[n]并苯、[n]并菲咯嗪、Schlüter 带和 Vögtle 带。它们的吸引力首先源于其独特的共轭性质,具有径向取向的 p 轨道,而不是垂直于大环的平面。其次,由于芳香带是不同手性的碳纳米管的模型化合物,因此在这些化合物中构建结构应变的合成策略最终可能为碳纳米管的合理化学合成开辟一条途径。这些化合物的难以捉摸性激发了过去几十年引人入胜和巧妙的合成策略。各种策略按其构建结构应变的方法进行分类,这是制备这些弯曲多芳烃的主要障碍。

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