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Thiol-ene Clickable Hyperscaffolds Bearing Peripheral Allyl Groups

Roy, Raj Kumar and Ramakrishnan, S (2011) Thiol-ene Clickable Hyperscaffolds Bearing Peripheral Allyl Groups. In: Journal of Polymer Science Part A: Polymer Chemistry, 49 (8). pp. 1735-1744.

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/pola.24...


Radical catalyzed thiol-ene reaction has become a useful alternative to the Huisgen-type click reaction as it helps to expand the variability in reaction conditions as well as the range of clickable entities. Thus, direct generation of hyper-branched polymers bearing peripheral allyl groups that could be clicked using a variety of functional thiols would be of immense value. A specifically designed AB(2) type monomer, that carries two allyl benzyl ethers groups and one alcohol functionality, was shown to undergo self-condensation under acid-catalyzed melt-transetherification to yield a hyperbranched polyether that carries numerous allyl end-groups. Importantly, it was shown that the kinetics of polymerization is not dramatically affected by the change of the ether unit from previously studied methyl benzyl ether to an allyl benzyl ether. The peripheral allyl groups were readily clicked quantitatively, using a variety of thiols, to generate an hydrocarbon-soluble octadecyl-derivative, amphiphilic systems using 2-mercaptoethanol and chiral amino acid (N-benzoyl cystine) derivatized hyperbranched structures; thus demonstrating the versatility of this novel class of clickable hyperscaffolds. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49:1735-1744, 2011

Item Type: Journal Article
Additional Information: Copyright of this article belongs to John Wiley and Sons.
Keywords: functionalization of polymers;glass transition; hyperbranched;kinetics (polym.);polyethers; thermogravimetric analysis (TGA)
Department/Centre: Division of Chemical Sciences > Inorganic & Physical Chemistry
Depositing User: Id for Latest eprints
Date Deposited: 20 Apr 2011 05:33
Last Modified: 20 Apr 2011 05:33
URI: http://eprints.iisc.ac.in/id/eprint/36737

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