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

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-ass...

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Bibliographic Details
Published in:Polymer bulletin (Berlin, Germany) Germany), 2011-11, Vol.67 (8), p.1483-1498
Main Authors: Türkan, Ali, Yılmaz, Faruk, Küçük, Asuman Çelik, Özdemir, Yusuf
Format: Article
Language:English
Subjects:
Applied sciences
Bulk polymerization
Characterization and Evaluation of Materials
Chemical synthesis
Chemistry
Chemistry and Materials Science
Complex Fluids and Microfluidics
Copolymers
Electrodes
Electrolytes
Enzymes
Exact sciences and technology
Lipase
Molecular weight
NMR
Nuclear magnetic resonance
Organic Chemistry
Organic polymers
Original Paper
Physical Chemistry
Physical properties
Physicochemistry of polymers
Polycaprolactone
Polymer Sciences
Polymerization
Polymers
Polymers and radiations
Preparation, kinetics, thermodynamics, mechanism and catalysts
Ring opening polymerization
Soft and Granular Matter
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Summary: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 1 H and 13 C 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.
ISSN:0170-0839
1436-2449
DOI:10.1007/s00289-011-0467-2