Thiol-ene clickable hyperscaffolds bearing peripheral allyl groups

Roy, Raj Kumar ; Ramakrishnan, S. (2011) Thiol-ene clickable hyperscaffolds bearing peripheral allyl groups Journal of Polymer Science Part A: Polymer Chemistry, 49 (8). pp. 1735-1744. ISSN 0887-624X

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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 hyperbranched polymers bearing peripheral allyl groups that could be clicked using a variety of functional thiols would be of immense value. A specifically designed AB2 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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Functionalization of Polymers; Glass Transition; Hyperbranched; Kinetics(polym.); Polyethers; Thermogravimetric Analysis (TGA)
ID Code:67218
Deposited On:29 Oct 2011 12:07
Last Modified:29 Oct 2011 12:07

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