Kołodziejski Michał, Stefankiewicz Artur R, Lehn Jean-Marie
Laboratory of Supramolecular Chemistry , Institut de Science et d'Ingénierie Supramoléculaires (ISIS) , UMR 7006 , CNRS , Université de Strasbourg , 8 allée Gaspard Monge , 67000 Strasbourg , France . Email:
Faculty of Chemistry , Adam Mickiewicz University , Umultowska 89b , 61-614 Poznań , Poland . Email:
Chem Sci. 2018 Dec 12;10(6):1836-1843. doi: 10.1039/c8sc04598d. eCollection 2019 Feb 14.
Self-assembling macrobicyclic cryptand-type organic cages display remarkable self-sorting behavior with efficient component selection. Making use of the dynamic covalent chemistry approach, eight different cages were synthesized by condensation of tris(2-aminopropyl)amine with structurally different dialdehydes. A series of self-sorting experiments were first carried out on simple dynamic covalent libraries. They reveal the influence of different structural features of the aldehyde components on the condensation with two triamine capping units. Subsequently, self-sorting experiments were performed on more complex systems involving several dialdehyde building blocks. Altogether, the results obtained describe the effect of the presence of a heteroatom, of electrostatic interactions, of delocalization and of the flexibility/stiffness of the propensity of a component to undergo formation of a macrobicyclic cage. In the presence of a catalytic amount of acid, the macrobicyclic structure undergoes dynamic component exchange.
自组装大环穴醚型有机笼合物表现出显著的自分类行为及高效的组分选择。利用动态共价化学方法，通过三（2-氨丙基）胺与结构不同的二醛缩合合成了八种不同的笼合物。首先在简单的动态共价文库上进行了一系列自分类实验。这些实验揭示了醛组分不同结构特征对与两个三胺封端单元缩合的影响。随后，在涉及多个二醛构建块的更复杂体系上进行了自分类实验。总体而言，所获得的结果描述了杂原子的存在、静电相互作用、离域作用以及组分形成大环笼合物倾向的柔韧性/刚性所产生的影响。在催化量的酸存在下，大环结构会发生动态组分交换。
