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首页> 外文期刊>Chemistry: A European journal >A [2]Catenane and a [2]Rotaxane as Prototypes of Topological and Euclidean Molecular 'Rubber Gloves'
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A [2]Catenane and a [2]Rotaxane as Prototypes of Topological and Euclidean Molecular 'Rubber Gloves'

机译：作为拓扑和欧几里得分子“橡胶手套”的原型的[2]壬烷和[2]轮烷。

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A [2]catenane and a [2]rotaxane have been prepared from a C_2-symmetric, 2,9-diphenyl-1,10-phenanthroline-based (dpp-based) macrocycle incorporating a 1,5-dioxynaphthalene subunit by means of the transition metal templated technique. In the case of the catenane, this macrocycle is interlocked with a dpp-based macrocycle that is oriented through the location of a p-tolyl substituent in the 4-position of the phenanthroline subunit. In the case of the rotaxane, the C_2-symmetric macrocycle is threaded onto an oriented, dumbbell-shaped molecule, based on the same 4-p-tolyl-1,10-phenanthroline subunit, which bears tetraarylmethane stoppers. Both species are chemically achiral molecules, yet they are composed entirely of asymmetric, mirror-image conformations. Conformational enantiomerization processes therefore take place exclusively by chiral pathways, conferring on these molecules the "rubber glove" property. However, while the molecular graph (constitutional formula) of the [2]rotaxane can be deformed into a planar and, hence, rigidly achiral representation, a feature shared by a few other compounds in the literature that have been characterized as "Euclidean rubber gloves", the molecular graph of the [2]catenane cannot be deformed in this way. It therefore has the unique property of being a chemically achiral "topological rubber glove".
机译：[2] catenane和[2] rotaxane已通过C_2-对称的2,9-二苯基-1,10-菲咯啉基（dpp基）大环化合物通过1,5-二氧萘亚基的结合而制备。过渡金属模板化技术。在链烷烃的情况下，该大环与基于dpp的大环互锁，该环通过对甲苯基取代基在菲咯啉亚基的4位上定位。在轮烷的情况下，基于相同的4-对甲苯基-1,10-菲咯啉亚基，C_2对称的大环被连接到一个定向的哑铃状分子上，该亚基带有四芳基甲烷塞。两种都是化学非手性分子，但它们完全由不对称的镜像构象组成。因此，构象对映异构化过程仅通过手性途径进行，赋予这些分子“橡胶手套”性质。但是，尽管[2]轮烷的分子图（组成式）可以变形为平面，因此可以刚性地形成非手性的表现形式，但文献中一些其他化合物共有的特征是“欧几里得橡胶手套”。 ”，[2]联烷烃的分子图不能以这种方式变形。因此，它具有作为化学非手性“拓扑橡胶手套”的独特性能。

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