N-Substituted Azacalixphyrins: Synthesis, Properties, and Self-Assembly

Zhongrui Chen (1) , Rose Haddoub , Jerome Mahe , Gabriel Marchand , Denis Jacquemin (2, 3) , Judicaelle Andeme Edzang (1) , Gabriel Canard (1) , Daniel Ferry (1) , O. Grauby (1) , Alain Ranguis (1) , Olivier Siri (1)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille
2 IUF - Institut universitaire de France
3 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

Pre- and postintroduction of substituents with respect to the macrocyclization step leads to previously unknown N-substituted azacalixphyrins. The stepwise synthetic approach has been studied in detail to highlight the key role of the N-substituents of the precursors and/or intermediates in terms of reactivity. Based on a combined experimental and theoretical investigation, the relationship between the properties of the macrocycles and their degree of substitution is rationalized. Depending on the nature of the N-substituents, the formation of supramolecular ribbon-like structures could also be observed, as demonstrated by combined TEM, SEM, AFM, and FTIR experiments.

Domaines: Chimie

Zhongrui Chen, Rose Haddoub, Jerome Mahe, Gabriel Marchand, Denis Jacquemin, et al.. N-Substituted Azacalixphyrins: Synthesis, Properties, and Self-Assembly. Chemistry - A European Journal, 2016, 22 (49), pp.17820-17832. ⟨10.1002/chem.201602288⟩. ⟨hal-01459072⟩