Greciano Elisa E, Matarranz Beatriz, Sánchez Luis
Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, Ciudad Universitaria s/n, 28040, Madrid, Spain.
Angew Chem Int Ed Engl. 2018 Apr 16;57(17):4697-4701. doi: 10.1002/anie.201801575. Epub 2018 Mar 14.
Studies were carried out on the hierarchical self-assembly versus pathway complexity of N-annulated perylenes 1-3, which differ only in the nature of the linking groups connecting the perylene core and the side alkoxy chains. Despite the structural similarity, compounds 1 and 2 exhibit noticeable differences in their self-assembly. Whereas 1 forms an off-pathway aggregate I that converts over time (or by addition of seeds) into the thermodynamic, on-pathway product, 2 undergoes a hierarchical process in which the kinetically trapped monomer species does not lead to a kinetically controlled supramolecular growth. Finally, compound 3, which lacks the amide groups, is unable to self-assemble under identical experimental conditions and highlights the key relevance of the amide groups and their position to govern the self-assembly pathways.
对萘并苝1 - 3的分层自组装与路径复杂性进行了研究，它们仅在连接苝核与侧链烷氧基的连接基团性质上有所不同。尽管结构相似，但化合物1和2在自组装过程中表现出显著差异。化合物1形成了一种非路径聚集体I，该聚集体会随时间（或通过添加晶种）转化为热力学上的路径产物，而化合物2则经历了一个分层过程，其中动力学捕获的单体物种不会导致动力学控制的超分子生长。最后，缺乏酰胺基团的化合物3在相同实验条件下无法自组装，这突出了酰胺基团及其位置对控制自组装途径的关键作用。
