Chemistry Department, Memorial University, St. John's, NL, CanadaA1B 3X7.
Chem Soc Rev. 2015 Sep 21;44(18):6494-518. doi: 10.1039/c5cs00274e. Epub 2015 May 29.
Cyclophanes have been firmly entrenched as a distinct class of compounds for well over half a century. The two main factors that have kept this field of chemistry going so strongly for such a long time are tremendous structural diversity and the interesting behaviour that is often observed. Although a very large number cyclophanes has been reported, only a very small proportion of them contain polycyclic aromatic systems that can be thought of as "large", i.e. with ≥4 rings. This Review puts the spotlight on such cyclophanes, illuminating both the chemistry that was used to synthesize them and what was learned from studying them. Context for the main body is provided by the careful consideration of the anatomy of a cyclophane and the classification of general synthetic approaches. The subsequent sections cover eleven different PAHs and are organized primarily according to increasing size of the aromatic system, starting with pyrene (C16, the only large polycyclic aromatic system to have been incorporated into numerous cyclophanes) and ending with hexabenzo[bc,ef,hi,kl,no,qr]coronene (C42).
环芳烷作为一类独特的化合物已经确立了半个多世纪。这个化学领域能够如此长时间地保持如此强劲发展的两个主要因素是巨大的结构多样性和经常观察到的有趣行为。尽管已经报道了大量的环芳烷，但其中只有很小一部分包含可以被认为是“大”的多环芳烃系统，即具有≥4 个环。这篇综述重点介绍了这些环芳烷，既阐明了用于合成它们的化学，也阐明了从研究它们中学到的东西。通过仔细考虑环芳烷的解剖结构和一般合成方法的分类，为正文提供了背景。随后的部分涵盖了十一种不同的多环芳烃，主要根据芳香体系的大小进行组织，从苝（C16，是唯一被大量环芳烷包含的大环多环芳烃系统）开始，以六苯并[bc,ef,hi,kl,no,qr] coronene（C42）结束。
