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.
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http://dx.doi.org/10.1002/chem.201602288 | DOI Listing |
Chemistry
December 2016
Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
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