(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.
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.
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|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|
|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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