Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly
Flexible imidazolium macrocycles: building blocks for anion-induced self-assembly
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柔性咪唑大环化合物：阴离子诱导自组装的构建模块
DOI：
10.1039/c7cc04661h
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发表时间：
2017
影响因子：
4.9
通讯作者：
Gong Han-Yuan
中科院分区：
文献类型：
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作者：
Yang Yu-Dong;Sessler Jonathan L.;Gong Han-Yuan
本文综述了近年来作者在阴离子诱导超分子自组装领域的研究成果。它是基于一组四聚咪唑大环的化学性质，特别是所谓的“德克萨斯大小”分子盒，环[2]（2,6-二（1h -咪唑-1-基）吡啶）[2]（1,4-二亚苯）（14+），及其同构体，环b[2]（2,6-二（1h -咪唑-1-基）吡啶）[2]（1,2-二亚苯）（24+），环[2]（2,6-二（1h -咪唑-1-基）吡啶）[2]（1,3-二亚苯）（34+）和环[2]（2,6-二（1h -咪唑-1-基）吡啶）[2]（2,6-二（1h -咪唑-1-基）吡啶）（44+）。这些系统已被证明是与有机羧酸盐或磺酸盐阴离子以及底物（例如，中性分子或金属阳离子）相互作用的通用构建块。迄今为止，大多数工作都是使用14+进行的，该系统已被发现支持构建许多刺激响应自组装集合。这个大环和其他“德克萨斯大小”盒子家族也显示出作为碳前体反应的潜力，并经过合成后修饰（PSM）产生新的功能大环，如反式和顺式环[2]((Z)- n- （2-（（6-（1h -咪唑-1-基）吡啶-2-基）氨基）乙烯基）甲酰胺[2]（1,4-二甲基苯）（分别为52+和62+）。在本文综述的基础上，我们提出咪唑大环14+ -44 +可以被认为是构建具有环境响应特征的集成体的有用工具，包括对自组装的控制和前体特异性PSM的能力。
This feature article summarises recent contributions of the authors in the area of anion-induced supramolecular self-assembly. It is based on the chemistry of a set of tetracationic imidazolium macrocycles, specifically the so-called ‘Texas-sized’ molecular box, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,4-dimethylenebenzene) (14+), and its congeners, cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,2-dimethylenebenzene) (24+), cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,3-dimethylenebenzene) (34+), and cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](2,6-dimethylenepyridine) (44+). These systems collectively have been demonstrated as being versatile building blocks that interact with organic carboxylate or sulfonate anions, as well as substrates (e.g., neutral molecules or metal cations). Most work to date has been carried out with 14+, a system that has been found to support the construction of a number of stimuli responsive self-assembled ensembles. This macrocycle and others of the ‘Texas-sized’ box family also show the potential to react as carbene precursors and to undergo post-synthetic modification (PSM) to produce new functional macrocycles, such as trans- and cis-cyclo[2]((Z)-N-(2-((6-(1H-imidazol-1-yl)pyridin-2-yl)amino)vinyl)formamide)[2](1,4-bismethylbenzene) (52+ and 62+, respectively). On the basis of the work reviewed in this Feature article, we propose that the imidazolium macrocycles 14+–44+ can be considered as useful tools for the construction of ensembles with environmentally responsive features, including control over self-assembly and an ability to undergo precursor-specific PSM.