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Five-component, one-pot synthesis of an electroactive rotaxane comprising a bisferrocene macrocycle.
Beilstein Journal of Organic Chemistry ( IF 2.2 ) Pub Date : 2020-06-30 , DOI: 10.3762/bjoc.16.128
Natalie Lagesse 1 , Luca Pisciottani 1 , Maxime Douarre 1 , Pascale Godard 1 , Brice Kauffmann 2 , Vicente Martí-Centelles 1 , Nathan D McClenaghan 1
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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.

中文翻译:


包含双二茂铁大环的电活性轮烷的五组分一锅法合成。



描述了通过与 1,4-双(氨基甲基)苯反应,对二茂铁接枝间苯二甲酸衍生物进行模板剪断以包围氢键轴。所得[2]轮烷的电活性大环成分是 Leigh 及其同事开发的多功能基准四酰胺变体的同系物。比较了不同氢键基序在轮烷和拟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。
更新日期:2020-06-30
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