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Synthesis and Characterization of Chiral [3,22]‐Ionenes
Author(s) -
Bazito Reinaldo C.,
Cássio Fernando L.,
Quina Frank H.
Publication year - 2005
Publication title -
macromolecular symposia
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.257
H-Index - 76
eISSN - 1521-3900
pISSN - 1022-1360
DOI - 10.1002/masy.200551124
Subject(s) - cyclodextrin , pyrene , tosyl , chemistry , aqueous solution , micelle , fluorescence , organic chemistry , demethylation , polymer chemistry , stereochemistry , biochemistry , physics , gene expression , quantum mechanics , dna methylation , gene
Summary: Two [3,22]‐ionenes with pendent chiral groups, glucopyranosyl‐[3,22]‐ionene and β‐cyclodextrin‐[3,22]‐ionene, were synthesized by the reaction between the tosyl derivatives of the carbohydrate (methyl alpha‐glucopyranoside or beta‐cyclodextrin) and the tertiary [3,22]‐polyamine obtained by selective demethylation of [3,22]‐ionene. The derivatives were characterized by 1 H NMR spectroscopy, presenting degrees of substitution of 30 and 45% for the glucosyl and cyclodextrin derivatives, respectively. It was shown by using pyrene as the fluorescent probe, that both polymers form hydrophobic domains, characteristic of micelle‐mimetic polysoaps in aqueous solution.