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One-pot two-step lipase-catalyzed synthesis of α,ω-thiophene-capped poly(ε-caprolactone) macromonomers and their use in electropolymerization

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Abstract

Macromonomers based on poly(ε-caprolactone) (PCL) with α,ω-thiophene functional end groups were prepared in bulk by enzymatic polymerization using immobilized Candida Antarctica lipase B (Novozym 435) as the catalyst. In the synthesis strategy, 3-thiophenemethanol was used to initiate the enzyme-assisted ring-opening polymerization of ε-caprolactone (ε-CL) to yield PCL with α-thiophene end group (initiation reaction, ThPCL) and then 3-thiopheneacetic acid was added to prepolymerized ε-CL to introduce ω-thiophene functionality in termination step (ThPCLTh). Macromonomers were characterized by 1H and 13C NMR, FTIR, and GPC. Moreover, the obtained macromonomers were employed in electropolymerization experiments and copolymers with thiophene or pyrrole were synthesized through their end thiophene groups. These polymers were characterized by cyclic voltammetry (CV), FTIR, and scanning electron microscopy (SEM). Conductivity measurements were carried out by the four-probe technique.

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Authors and Affiliations

  1. Department of Chemistry, Gebze Institute of Technology, 41400, Gebze, Kocaeli, Turkey

    Ali Türkan, Faruk Yılmaz, Asuman Çelik Küçük & Yusuf Özdemir

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  1. Ali Türkan
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  2. Faruk Yılmaz
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  3. Asuman Çelik Küçük
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Correspondence to Faruk Yılmaz.

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Türkan, A., Yılmaz, F., Küçük, A.Ç. et al. One-pot two-step lipase-catalyzed synthesis of α,ω-thiophene-capped poly(ε-caprolactone) macromonomers and their use in electropolymerization. Polym. Bull. 67, 1483–1498 (2011). https://doi.org/10.1007/s00289-011-0467-2

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  • DOI: https://doi.org/10.1007/s00289-011-0467-2

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