Helical supramolecular polymerization of C3-symmetric amides and retroamides: on the origin of cooperativity and handedness

Julia Buendía; Joaquín Calbo; Fátima García; Juan Aragó; Pedro M. Viruela; Enrique Ortí; Luis Sánchez

doi:10.1039/C6CC02681H

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Helical supramolecular polymerization of C₃-symmetric amides and retroamides: on the origin of cooperativity and handedness†‡

Julia Buendía,§^a Joaquín Calbo,§^b Fátima García,^a Juan Aragó,^b Pedro M. Viruela,^b Enrique Ortí*^b and Luis Sánchez*^a

Author affiliations

* Corresponding authors

^a Departamento de Química Orgánica, Facultad de Ciencias Químicas, Ciudad Universitaria s/n, 28040 Madrid, Spain
E-mail: lusamar@quim.ucm.es

^b Instituto de Ciencia Molecular, Universidad de Valencia, 46980 Paterna, Spain
E-mail: enrique.orti@uv.es

Abstract

The cooperative supramolecular polymerization of 1 and 2 yields P- or M-type helical aggregates depending on the absolute configuration (S or R) of the stereogenic centres attached to the side chains. The connectivity of the amide group does not affect the handedness of the helical aggregates, but determines a larger cooperativity for retroamides 1.

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Article information

DOI: https://doi.org/10.1039/C6CC02681H
Article type: Communication
Submitted: 30 Mar 2016
Accepted: 22 Apr 2016
First published: 25 Apr 2016

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Chem. Commun., 2016,52, 6907-6910

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Helical supramolecular polymerization of C₃-symmetric amides and retroamides: on the origin of cooperativity and handedness

J. Buendía, J. Calbo, F. García, J. Aragó, P. M. Viruela, E. Ortí and L. Sánchez, Chem. Commun., 2016, 52, 6907 DOI: 10.1039/C6CC02681H

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