Tautz Markus, Torras Juan, Grijalvo Santiago, Eritja Ramón, Saldías César, Alemán Carlos, Díaz David Díaz
Institut für Organische Chemie, Universität Regensburg Universitätsstr. 31 93053 Regensburg Germany
Departament d'Enginyeria Química, EEBE, Universitat Politècnica de Catalunya C/Eduard Maristany, 10-14, Ed. 12 08019 Barcelona Spain.
RSC Adv. 2019 Jul 3;9(36):20841-20851. doi: 10.1039/c9ra03316e. eCollection 2019 Jul 1.
Gelation of organic solvents using ,'-((1,2)-cyclohexane-1,2-diyl)didodecanamide (C-Cyc) is driven by its self-assembly antiparallel hydrogen bonds and van der Waals intermolecular interactions. In this work we carried out a dual isosteric substitution of the two amide groups with 1,2,3-triazole rings affording the corresponding isosteric gelator (click-C-Cyc). A detailed comparative study in terms of the gelation ability and gel properties demonstrated that the 1,2,3-triazoles can take over all of the functions derived from the amide groups offering a versatile strategy for tuning the properties of the corresponding gels. This is not an obvious outcome because the directional amide groups in C-Cyc constitute the source of the hydrogen bonds to build the 3D self-assembled network. Furthermore, theoretical calculations revealed that click-C-Cyc can adopt a wide variety of interacting patterns, whose relative stability depends on the polarity of the environment, this is in good agreement with the experimental data obtained regarding its gelation ability. Other important features of click-C-Cyc for potential practical applications are its non-cytotoxic character and its phase-selective gelation of water-oil mixtures.
使用,'-((1,2)-环己烷-1,2-二基)二癸酰胺(C-Cyc)使有机溶剂凝胶化是由其自组装反平行氢键和范德华分子间相互作用驱动的。在这项工作中，我们用1,2,3-三唑环对两个酰胺基团进行了双重等排取代，得到了相应的等排凝胶剂(click-C-Cyc)。关于凝胶化能力和凝胶性质的详细比较研究表明，1,2,3-三唑可以承担所有源自酰胺基团的功能，为调节相应凝胶的性质提供了一种通用策略。这并非显而易见的结果，因为C-Cyc中的定向酰胺基团构成了构建三维自组装网络的氢键来源。此外，理论计算表明，click-C-Cyc可以采用多种相互作用模式，其相对稳定性取决于环境的极性，这与关于其凝胶化能力的实验数据高度吻合。click-C-Cyc在潜在实际应用中的其他重要特性是其无细胞毒性以及对水油混合物的相选择性凝胶化。
