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One pot biocatalytic synthesis of a biodegradable electroactive macromonomer based on 3,4-ethylenedioxytiophene and poly(L-lactic acid)

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바이오화학분류
    • 바이오플라스틱
      1. 플라스틱
    • 바이오정밀화학
      1. 기타
    • 화장품용 기능성소재
      1. 계면활성제⁄증점제
    • 의료용 화학소재
      1. 치료제
      2. 식품첨가제
논문

One pot biocatalytic synthesis of a biodegradable electroactive macromonomer based on 3,4-ethylenedioxytiophene and poly(L-lactic acid)

학술지

Materials science & engineering. C, Materials for biological applications

저자명

da Silva, Aruã C.; Augusto, Tatiana; Andrade, Leandro H.; Có rdoba de Torresi, Susana I.

초록

<P><B>Abstract</B></P> <P>A novel electroactive macromonomer based on poly(<SMALL>L</SMALL>-lactic acid) (PLLA) with (3,4-ethylenedioxythiophene) (EDOT) functional end groups, was prepared by a traditional approach of organometallic polymerization with stannous octanoate [Sn(oct<SUB>2</SUB>)] and enzymatic polymerization using immobilized <I>Candida antarctica</I> Lipase B (CAL-B) and Amano lipase <I>Pseudomonas cepacia</I>(PS-IM), as catalysts. In the synthetic strategy, (2,3-dihydrothieno[3,4-b] dioxin-2-yl)methanol (EDOT-OH) was used to initiate the ring opening polymerization of lactide to yield PLLA with EDOT end group. All macromonomers (EDOT-PLLA) were characterized by <SUP>1</SUP>H and <SUP>13</SUP>C RMN, MALDI-TOF, GPC and EDX. Moreover, ICP-OES analysis showed the presence of Sn traces in the material synthesized by the traditional approach, but that pathway led to macromonomers with higher molecular weight while the enzymatic route led to completely metal-free macromonomers with medium and lower molecular weights. Also, electrochemical and chemical polymerization of EDOT-PLLA were tested showing that it is possible to prepare degradable conducting polymers based on poly(3,4-ethylenedioxythiphene) (PEDOT). The biocatalytic synthesis is a very promising and environmental friendly pathway for the preparation of biodegradable materials for short time applications.</P> <P><B>Highlights</B></P> <P> <UL> <LI> One step enzymatic pathway synthesis of degradable electroactive macromonomers. </LI> <LI> Enzymatic route leads to metal-free macromonomers. </LI> <LI> EDOT-PLLA macromonomers can be copolymerized with EDOT by oxidation. </LI> <LI> Degradable and conducting PEDOT copolymers suitable for biomedical applications. </LI> </UL> </P>

발행연도

2018

발행기관

Elsevier

ISSN

0928-4931

ISSN

1873-0191

83

페이지

pp.35-43

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논문; 2018-12-31

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