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Cyclodextrins in Polymer Modification: Diels–Alder Addition of Cyclopentadiene/Methylated‐ β ‐Cyclodextrin Complex on Unsaturated Polyester and Formation of a New Type of Polypseudorotaxane
Author(s) -
Alupei Valentina,
Alupei Iulian C.,
Ritter Helmut
Publication year - 2005
Publication title -
macromolecular rapid communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.348
H-Index - 154
eISSN - 1521-3927
pISSN - 1022-1336
DOI - 10.1002/marc.200400442
Subject(s) - cyclopentadiene , polyester , moiety , ethylene glycol , cyclodextrin , maleic anhydride , diels–alder reaction , polymer chemistry , cyclohexene , chemistry , materials science , organic chemistry , polymer , copolymer , catalysis
Summary: Cyclopentadiene ( 1 ) was incorporated as a guest into the cavity of randomly methylated‐ β ‐cyclodextrin (me‐ β ‐CD) as a host, yielding the stable, water compatible cyclopentadiene/me‐ β ‐CD complex ( 1a ). We successfully attempted to use the synthesised complex in a Diels–Alder addition with a water‐soluble unsaturated polyester ( 2 ) derived from poly(ethylene glycol) and maleic anhydride. The reaction yielded a new type of polypseudorotaxane ( 3 ). Examination of the polypseudorotaxane ( 3 ) and a model inclusion complex of the starting unsaturated polyester with me‐ β ‐CD ( 2a ) showed that cyclodextrins are threaded onto the main chain in both cases. The cyclohexene moiety formed after the Diels–Alder addition does not act as a stopper, a dethreading process being evidenced and discussed.The polypseudorotaxane synthesized here.