Collect. Czech. Chem. Commun. 2003, 68, 1131-1140

Synthesis of Polylactide with Thiol End Groups

Štěpán Popelkaa,b,* and František Rypáčeka,b

a Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, Heyrovského nám. 2, CZ 162 06 Prague 6, Czech Republic
b Center for Cell Therapy and Tissue Repair, Charles University, 2nd Faculty of Medicine, Institute of Neurosciences, V Úvalu 84, 150 18, Prague 5, Czech Republic


Four synthetic routes to poly(L-lactide) with thiol end groups based on ring-opening polymerization of L-lactide (LA) catalysed with tin(II) 2-ethylhexanoate (Sn(Oct)2) are reported. The following alcohols were used as co-initiators of polymerization: 2-sulfanylethan-1-ol, 2-[(2,4-dinitrophenyl)sulfanyl]ethan-1-ol, 2-(tritylsulfanyl)ethan-1-ol and allyl alcohol. End groups introduced into polymers by co-initiators were transformed to thiol groups by a subsequent modification reaction. The efficiencies of the used synthetic methods were evaluated and discussed. The best results were obtained with co-initiator 2-(tritylsulfanyl)ethan-1-ol.

Keywords: Polylactides; Thiol-functionalized polymers; End group modification; Thiols; Ring-opening polymerizations; Adsorption on gold.

References: 16 live references.