Heterobifunctional poly(ε-caprolactone): Synthesis of α-cholesterol-ω-pyrene PCL via combination of ring-opening polymerization and “click” chemistry

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• 作者：Sevinc Ilkar Erdagi^a ; Erdinc Doganci^b ; ^c ; Cavit Uyanik^a ; ^{cuyanik@kocaeli.edu.tr" class="auth_mail" title="E-mail the corresponding author} ; Faruk Yilmaz^b ; ^{fyilmaz@gyte.edu.tr" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Poly(ε-caprolactone) ; Ring-opening polymerization ; Click chemistry ; Cholesterol ; Pyrene
• 刊名：Reactive and Functional Polymers
• 出版年：2016
• 出版时间：February 2016
• 年：2016
• 卷：99
• 期：Complete
• 页码：49-58
• 全文大小：1598 K

文摘

A well-defined novel α-cholesterol and ω-pyrene heterobifunctional poly(ε-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 ε-caprolactone (ε-CL) to prepare α-cholesterol-ω-hydroxy PCL polymer (Chol-PCL-OH). ω-Hydroxy functionality of Chol-PCL-OH was then successfully converted into bromide and azide. Further end-group modification of ω-azide poly(ε-caprolactone) (Chol-PCL-N₃) was achieved quantitatively by copper (I)-catalyzed cycloaddition of azide functional group and 1-ethynyl pyrene, which led to the desired PCL with α-cholesterol and ω-pyrene groups (Chol-PCL-Pyr). The effect of molar ratio of ε-CL to the initiator on the molecular weight of the obtained Chol-PCL-Pyr was also investigated.