N‐Substituted Azacalixphyrins: Synthesis,Properties, and Self‐Assembly |
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Authors: | Dr. Zhongrui Chen Dr. Rose Haddoub Jérôme Mahé Dr. Gabriel Marchand Prof. Denis Jacquemin Dr. Judicaelle Andeme Edzang Dr. Gabriel Canard Dr. Daniel Ferry Dr. Olivier Grauby Alain Ranguis Dr. Olivier Siri |
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Affiliation: | 1. Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), Marseille, France;2. CEISAM UMR CNRS 6230, Université de Nantes, Nantes Cedex 3, France;3. Institut Universitaire de France, Paris Cedex 05, France |
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Abstract: | 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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Keywords: | aromaticity azacalixphyrins macrocycles substituent effects structure– activity relationships |
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