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Title

Aqueous micro and nanoreactors based on alternating copolymers of phenylmaleimide and vinylpyrrolidone bearing pendant l-proline stabilized with PEG grafted chains

AuthorsPrado, Anselmo del ; Pintado-Sierra, Mercedes ; Juan-Y-Seva, Marta; Navarro, Rodrigo; Reinecke, Helmut ; Rodríguez-Hernández, Juan ; Elvira, Carlos ; Fernández-Mayoralas, Alfonso ; Gallardo, Alberto
KeywordsStimuli-sensitive polymers
Functionalization of polymers
Catalysis
Radical polymerization
Copolymerization
Issue Date2017
PublisherJohn Wiley & Sons
CitationJournal of Polymer Science, Part A: Polymer Chemistry 55: 1228-1236 (2017)
AbstractProline may work efficiently in water as catalyst of aldol reactions if it is hydrophobically activated. In this work, we have maximized this hydrophobic activation by the preparation of linear alternating copolymers of hydrophobic phenylmaleimide and a vinylpyrrolidone derivative bearing proline. These copolymers were water soluble above pH 5.0 and, unlike the free proline, exhibited efficient catalysis at pH 7.0. Moreover, they catalyzed and presented enantioselectivity in an aggregated form at pH 4.0 (close to the isoelectric point, IEP, of the polymer). This enantioselectivity has been related to the exclusion of water at this IEP. To control the size and stabilize the aggregates, PEG grafted copolymers were prepared by the incorporation of a PEG-macromer (2–10 mol%), which rendered stable nano-aggregates in water at the IEP. At this pH they catalyzed the aldol reaction in a higher rate than the non-grafted polymer, but the enantioselectivity was decreased. © 2016 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 55, 1228–1236.
Publisher version (URL)http://dx.doi.org/10.1002/pola.28487
URIhttp://hdl.handle.net/10261/150160
DOI10.1002/pola.28487
Identifiersdoi: 10.1002/pola.28487
issn: 0887-624X
e-issn: 1099-0518
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