Issue 15, 2013

The importance of the amide configuration in the gelation process and topochemical polymerization of phenylacetylene macrocycles

Abstract

Two series of amide-containing phenylacetylene macrocycles (PAMs) were prepared and self-assembled through a gelation process in an organic solvent. Their gelation properties along with their molecular arrangements in the xerogel state, their morphological features and their reactivity toward the topochemical polymerization of the butadiyne units embedded within the structure were studied with respect to the amide configuration. The PAMs of series 1 with the nitrogen atom of the amide function directly attached to the phenyl groups of the PAMs (acetanilide derivatives) showed less organized molecular organization and less reactivity toward topochemical polymerization than the PAMs of series 2 with the inverted amide configuration (benzamide derivatives). The importance of the amide configuration in the gelation process was confirmed by theoretical calculations at the density functional theory level. Moreover, the computed architecture for molecules of series 1 was shown to be incompatible with topochemical reaction in agreement with experimental observation. The actual combination of experiments and calculations allows the design of larger covalently linked, rigid organic nanotubes.

Graphical abstract: The importance of the amide configuration in the gelation process and topochemical polymerization of phenylacetylene macrocycles

Supplementary files

Article information

Article type
Paper
Submitted
22 dec 2012
Accepted
11 feb 2013
First published
11 feb 2013

J. Mater. Chem. C, 2013,1, 2680-2687

The importance of the amide configuration in the gelation process and topochemical polymerization of phenylacetylene macrocycles

S. Rondeau-Gagné, J. R. Néabo, M. Desroches, K. Cantin, A. Soldera and J. Morin, J. Mater. Chem. C, 2013, 1, 2680 DOI: 10.1039/C3TC00917C

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements