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(Ultra)fast catalyst-free macromolecular conjugation in aqueous environment at ambient temperature

Glassner, Mathias, Delaittre, Guillaume, Kaupp, Michael, Blinco, James P., & Barner-Kowollik, Christopher (2012) (Ultra)fast catalyst-free macromolecular conjugation in aqueous environment at ambient temperature. Journal of the American Chemical Society, 134(17), pp. 7274-7277.

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Abstract

Tailor-made water-soluble macromolecules, including a glycopolymer, obtained by living/controlled RAFT-mediated polymerization are demonstrated to react in water with diene-functionalized poly(ethylene glycol)s without pre- or post-functionalization steps or the need for a catalyst at ambient temperature. As previously observed in organic solvents, hetero-Diels-Alder (HDA) conjugations reached quantitative conversion within minutes when cyclopentadienyl moieties were involved. However, while catalysts and elevated temperatures were previously necessary for open-chain diene conjugation, additive-free HDA cycloadditions occur in water within a few hours at ambient temperature. Experimental evidence for efficient conjugations is provided via unambiguous ESI-MS, UV/vis, NMR, and SEC data.

Impact and interest:

10 citations in Scopus
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9 citations in Web of Science®

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ID Code: 51005
Item Type: Journal Article
Keywords: Aqueous environment, Catalyst-free, Cycloadditions, Cyclopentadienyls, Elevated temperature, Experimental evidence, Glycopolymers, Hetero-diels-Alder, RAFT-mediated polymerization, Cycloaddition, Directive antennas, Macromolecules, Olefins, Organic solvents, Polyethylene glycols, Temperature, Catalysts, cyclopentadiene derivative, macrogol, water, aqueous solution, article, catalyst, chemical reaction, conjugation, controlled study, environmental temperature, gel permeation chromatography, macromolecule, molecular weight, nuclear magnetic resonance, polymerization, stoichiometry, ultraviolet radiation
DOI: 10.1021/ja301762y
ISSN: 0002-7863
Subjects: Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000)
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 05 Jul 2012 08:26
Last Modified: 13 Jun 2013 00:51

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