Caprice Kenji, Pupier Marion, Kruve Anneli, Schalley Christoph A, Cougnon Fabien B L
Department of Organic Chemistry , University of Geneva , 30 Quai Ernest Ansermet , 1211 Geneva 4 , Switzerland . Email:
Institut für Chemie und Biochemie , Freie Universität Berlin , Takustraße 3 , 14195 Berlin , Germany.
Chem Sci. 2017 Dec 18;9(5):1317-1322. doi: 10.1039/c7sc04901c. eCollection 2018 Feb 7.
We report the efficient condensation of imine-based macrocycles from dialdehyde and aliphatic diamines in pure water. Within the libraries, we identified a family of homologous amphiphilic [2]catenanes, whose self-assembly is primarily driven by the hydrophobic effect. The length and odd-even character of the diamine alkyl linker dictate both the yield and the conformation of the [2]catenanes, whose particular thermodynamic stability further shifts the overall equilibrium in favour of imine condensation. These findings highlight the role played by solvophobic effects in the self-assembly of complex architectures.
我们报道了在纯水中由二醛和脂肪族二胺高效缩合生成基于亚胺的大环化合物。在这些化合物库中，我们鉴定出了一类同系的两亲性[2]连环烷，其自组装主要由疏水作用驱动。二胺烷基连接基的长度和奇偶特性决定了[2]连环烷的产率和构象，其特殊的热力学稳定性进一步使整体平衡向有利于亚胺缩合的方向移动。这些发现突出了疏溶剂效应在复杂结构自组装中所起的作用。
