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Synthesis and characterization of new aromatic polyamides bearing crown ethers and acyclic ethylene oxide units in the pendant structure. III. Benzo-18-crown-6 systems and their open-chain counterparts
Authors
Hugh D. Burrows
Verónica Calderón
+5 more
Félix García
José Miguel García
Gert Schwarz
María J. Tapia
Artur J. M. Valente
Publication date
1 January 2006
Publisher
'Wiley'
Doi
Cite
Abstract
We report the synthesis and characterization of 10 novel polyamides containing the benzo-18-crown-6 subunit and its dipodal counterpart, along with their properties, and a comparison with homologous polyamides bearing benzo-12-crown-4, benzo-15-crown-5, and the corresponding dipodal systems. The anomalous polymerization of some of the diacid monomers, that leads to insoluble gels under standard Yamazaki polymerization conditions, is described. The gel formation has been attributed to the threading of cyclic oligoamides with a growing polyamide chain to yield rotaxanes, polyrotaxanes, catenanes, or polycatenanes. Polyamide macrocycles have been characterized with matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. A route to avoid gel formation, consisting of a lower initial monomer concentration, is also described, along with the polymer properties of the polyamides obtained, including the chemical characterization, mechanical behavior, water sorption, morphology, diffusion data, and permeability of membranes prepared with these polymers. © 2006 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 44: 6252-6269, 200
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