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N‐Substituted Azacalixphyrins: Synthesis, Properties, and Self‐Assembly
Author(s) -
Chen Zhongrui,
Haddoub Rose,
Mahé Jérôme,
Marchand Gabriel,
Jacquemin Denis,
Andeme Edzang Judicaelle,
Canard Gabriel,
Ferry Daniel,
Grauby Olivier,
Ranguis Alain,
Siri Olivier
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201602288
Subject(s) - supramolecular chemistry , reactivity (psychology) , ribbon , chemistry , substitution (logic) , fourier transform infrared spectroscopy , self assembly , stereochemistry , crystallography , combinatorial chemistry , materials science , organic chemistry , chemical engineering , crystal structure , computer science , medicine , alternative medicine , pathology , programming language , composite material , engineering
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.