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Beijing National Laboratory for Molecular Sciences (BNLMS), Key Lab of Polymer Chemistry & Physics of Ministry of Education, College of Chemistry, Peking University, Beijing, China
; Fax: (+86) 10-6275-6660
; Tel: (+86) 10-6275-6660
Soft Matter, 2012,8, 5486-5492
01 Dec 2011,
14 Mar 2012
First published online
05 Apr 2012
A phenyl and a 2,3,5,6-tetrafluorophenyl ring, each bearing a tris(n-dodecyloxy)benzylamine moiety via an amide bond, were tethered together through an imine linkage to give a non-covalent synthon (imine 1) with a strong capacity of supramolecular self-assembly. Gelation was observed in several organic solutions, within which fibrous aggregate morphologies were visualized by SEM and AFM. Both arene–perfluoroarene stacking and amide–amide hydrogen bonding interactions were responsible for such self-assembly behaviours, as evidenced by 1H NMR studies. Hydrolysis of the imine linkage catalyzed by acid strongly weakened the intermolecular interactions, resulting in dissociation of the low molecular weight gelator and giving rise to an acid-mediated gel–sol transition.
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