Heterobifunctional poly(epsilon-caprolactone): Synthesis of alpha-cholesterol-omega-pyrene PCL via combination of ring-opening polymerization and "click" chemistry

Erdagi S. , Doganci E. , UYANIK C. , Yilmaz F.

REACTIVE & FUNCTIONAL POLYMERS, vol.99, pp.49-58, 2016 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 99
  • Publication Date: 2016
  • Doi Number: 10.1016/j.reactfunctpolym.2015.12.005
  • Page Numbers: pp.49-58


A well-defined novel alpha-cholesterol and omega-pyrene heterobifunctional poly(epsilon-caprolactone) (Chol-PCL-Pyr) was synthesized by a combination of ring-opening polymerization (ROP) and "click" chemistry techniques. A cholesterol compound with hydroxyl functional group was used as the initiator in the ROP of epsilon-caprolactone (epsilon-CL) to prepare alpha-cholesterol-omega-hydroxy PCL polymer (Chol-PCL-OH). omega-Hydroxy functionality of Chol-PCL-OH was then successfully converted into bromide and azide. Further end-group modification of omega-azide poly(epsilon-caprolactone) (Chol-PCL-N-3) was achieved quantitatively by copper (1)-catalyzed cycloaddition of azide functional group and 1-ethynyl pyrene, which led to the desired PCL with alpha-cholesterol and omega-pyrene groups (Chol-PCL-Pyr). The effect of molar ratio of epsilon-CL to the initiator on the molecular weight of the obtained CholPCL-Pyr was also investigated. (C) 2015 Elsevier B.V. All rights reserved.