H-Bonding-driven gel formation of a phenylacetylene macrocycle

Katy Cantin; Simon Rondeau-Gagné; Jules Roméo Néabo; Maxime Daigle; Jean-Francois Morin

doi:10.1039/C1OB05441D

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Organic & Biomolecular Chemistry

Issue 12, 2011

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H-Bonding-driven gel formation of a phenylacetylene macrocycle

Katy Cantin , Simon Rondeau-Gagné , Jules Roméo Néabo , Maxime Daigle and Jean-Francois Morin

Org. Biomol. Chem., 2011,9, 4440-4443

DOI: 10.1039/C1OB05441D
Received 21 Mar 2011, Accepted 19 Apr 2011
First published on the web 20 Apr 2011

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An amide-containing phenylacetylene macrocycle (PAM) has been synthesized and its gelation properties were studied in different solvents. Surprisingly, this macrocycle forms organogels at low concentration in many polar and apolar solvents. XRD and FTIR analysis suggest that this macrocycle forms stable supramolecular assemblies owing to H-bonding. Scanning electron microscopy analyses show the formation of bundles of nanofibrils, demonstrating the long-range organization of this material.