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首页> 外文期刊>Chemistry: A European journal >Exploiting Molecular Self-Assembly: From Urea-Based Organocatalysts to Multifunctional Supramolecular Gels
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Exploiting Molecular Self-Assembly: From Urea-Based Organocatalysts to Multifunctional Supramolecular Gels

机译：利用分子自组装：从基于尿素的有机催化剂到多功能超分子凝胶

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摘要

We describe the self-assembly properties of chiral N,N'-disubstituted urea-based organocatalyst 1 that leads to the formation of hierarchical supramolecular gels in organic solvents at low concentrations. The major driving forces for the gelation are hydrogen bonding and π-π interactions according to FTIR and ~1H NMR spectroscopy, as well as quantum-mechanical studies. The gelation scope could be interpreted based on Kamlet-Taft solvatochromic parameters. TEM, SEM, and AFM imaging revealed that a variety of morphologies including helical, laths, porous, and lamellar nanostructures could be obtained by varying the solvent. Experimental gelation tests and computational structural analysis of various structurally related compounds proved the existence of a unique set of molecular interactions and an optimal hydrophilic/hydrophobic balance in 1 that drive the formation of stable gels. Responses to thermal, mechanical, optical, and chemical stimuli, as well as multifunctionality were demonstrated in some model gel materials. Specifically, 1 could be used for the phase-selective gelation of organic solvent/water mixtures. The gel prepared in glycerol was found to be thixotropic and provided a sensitive colorimetric method for the detection of Ag~I ions at millimolar concentrations in aqueous solution. Moreover, the gel matrix obtained in toluene served as a nanoreactor for the Friedel-Crafts alkylation of 1H-indole with trans-b-nitrostyrene.
机译：我们描述了手性N，N'-二取代脲基有机催化剂1的自组装特性，该特性导致有机溶剂中低浓度下的分层超分子凝胶的形成。根据FTIR和〜1H NMR光谱以及量子力学研究，凝胶化的主要驱动力是氢键和π-π相互作用。凝胶作用的范围可以根据Kamlet-Taft溶剂变色参数来解释。 TEM，SEM和AFM成像表明，通过改变溶剂可以得到包括螺旋形，板条形，多孔和层状纳米结构在内的多种形态。各种结构相关化合物的实验胶凝测试和计算结构分析证明，存在着一组独特的分子相互作用和一种最佳的亲水/疏水平衡，可以驱动稳定的凝胶形成。在某些模型凝胶材料中证明了对热，机械，光学和化学刺激以及多功能的响应。具体而言，可将1用于有机溶剂/水混合物的相选择胶凝。发现在甘油中制备的凝胶具有触变性，并为检测水溶液中毫摩尔浓度的Ag〜I离子提供了灵敏的比色方法。而且，在甲苯中获得的凝胶基质用作1H-吲哚与反式-b-硝基苯乙烯的弗里德-克来福特烷基化的纳米反应器。

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