Synthesis of an Alkene-Containing Copolylactide and Its Facile Modification by the Addition of Thiols
journal contributionposted on 31.03.2016, 12:22 by Pranav P. Kalelkar, Guillermo R. Alas, David M. Collard
The ring-opening copolymerization of 3,6-bis(chloromethyl)-1,4-dioxane-2,5-dione and l-lactide affords a chloro-substituted polylactide copolymer (chloro-PL). Base-promoted dehydrochlorination of chloro-PL provides a copolymer (ene-PL) that contains electrophilic α,β-unsaturated ester units. The copolymer undergoes conjugate addition with a variety of thiols in solution under mildly basic conditions and also in the presence of AIBN. Reaction on the surface of films of the unsaturated copolyester is demonstrated by the addition of a thiol-substituted fluorescent dye.