title: N-Substituted Azacalixphyrins: Synthesis, Properties, and Self-Assembly.
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.
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Zhongrui
authors.initials: Z
authors.lastname: Chen
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Rose
authors.initials: R
authors.lastname: Haddoub
authors.affiliation: CEISAM UMR CNRS 6230, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.
authors.forename: Jérôme
authors.initials: J
authors.lastname: Mahé
authors.affiliation: CEISAM UMR CNRS 6230, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Marchand
authors.affiliation: CEISAM UMR CNRS 6230, Université de Nantes, 2 rue de la Houssinière, BP 92208, 44322, Nantes Cedex 3, France.|Institut Universitaire de France, 1, rue Descartes, 75231, Paris Cedex 05, France.
authors.forename: Denis
authors.initials: D
authors.lastname: Jacquemin
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Judicaelle
authors.initials: J
authors.lastname: Andeme Edzang
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Canard
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Daniel
authors.initials: D
authors.lastname: Ferry
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Grauby
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Alain
authors.initials: A
authors.lastname: Ranguis
authors.affiliation: Aix Marseille Université, CNRS UMR 7325, Centre Interdisciplinaire de Nanosciences de Marseille (CINaM), 13288, Marseille, France.
authors.forename: Olivier
authors.initials: O
authors.lastname: Siri
keywords: aromaticity; azacalixphyrins; macrocycles; structure-activity relationships; substituent effects