Lagesse Natalie, Pisciottani Luca, Douarre Maxime, Godard Pascale, Kauffmann Brice, Martí-Centelles Vicente, McClenaghan Nathan D
Institut des Sciences Moléculaires, CNRS UMR 5255, University of Bordeaux, Talence, France.
Institut Européen de Chimie et Biologie, CNRS UMS 3033, INSERM US001, University of Bordeaux, Pessac, France.
Beilstein J Org Chem. 2020 Jun 30;16:1564-1571. doi: 10.3762/bjoc.16.128. eCollection 2020.
The templated clipping of a ferrocene-grafted isophthalic acid derivative to encircle a hydrogen-bonding axle through the reaction with 1,4-bis(aminomethyl)benzene is described. The constituent electroactive macrocycle of the resultant [2]rotaxane is a homologue of the versatile benchmark tetraamide variant developed by Leigh and co-workers. The relative templating effect of different hydrogen-bonding motifs in rotaxane and pseudorotaxane generation is compared, with yields varying from 0 to 41%. The electrochemical properties and single crystal X-ray structure of a doubly ferrocene-decorated [2]rotaxane are further reported.
描述了通过与1,4-双（氨甲基）苯反应，对二茂铁接枝的间苯二甲酸衍生物进行模板剪裁以环绕氢键轴的过程。所得[2]轮烷的组成电活性大环是Leigh及其同事开发的通用基准四酰胺变体的同系物。比较了不同氢键基序在轮烷和准轮烷生成中的相对模板效应，产率从0%到41%不等。进一步报道了双二茂铁修饰的[2]轮烷的电化学性质和单晶X射线结构。
