Synthesis and characterization of regioregular poly(3-hexylthiophene) by Heck reaction

ZHANG Jie; LI Jian; SUN Minghui

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Synthesis and characterization of regioregular poly(3-hexylthiophene) by Heck reaction

更新时间：2025-12-10

- Synthesis and characterization of regioregular poly(3-hexylthiophene) by Heck reaction
- CIESC Journal Issue 6, Pages: 1587-1591(2010)
- 作者机构：
  
  常州大学材料科学与工程学院
- 作者简介：
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- Online First：05 June 2010，
  
  Published：05 June 2010
- 稿件说明：
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ZHANG Jie, LI Jian, SUN Minghui. Synthesis and characterization of regioregular poly(3-hexylthiophene) by Heck reaction[J]. CIESC Journal, 2010, (6): 1587-1591.
DOI：

ZHANG Jie, LI Jian, SUN Minghui. Synthesis and characterization of regioregular poly(3-hexylthiophene) by Heck reaction[J]. CIESC Journal, 2010, (6): 1587-1591. DOI：

摘要

采用Heck反应法合成了具有较高分子量和立构规整度的聚（3-己基噻吩）。研究了溶剂的种类及配比、相转移催化剂及催化剂的种类以及反应温度、反应时间对所得聚（3-己基噻吩）的分子量和规整度的影响。用凝胶色谱（GPC）和核磁共振谱（1H NMR）对聚（3-己基噻吩）的分子量及立构规整度进行了表征。用紫外-可见分光光度计和荧光分光光度计研究了聚（3-己基噻吩）的吸收光谱和发射光谱。结果表明，当溶剂为二甲基甲酰胺与四氢呋喃（DMF∶THF=1∶1）的混合溶剂，采用醋酸钯［用量为单体量的5%（摩尔分数）］为催化剂，四丁基溴化铵［用量为单体量的100%（摩尔分数)］为相转移催化剂时，在80℃下反应12 h所得聚（3-己基噻吩）的分子量可达6700，立构规整度超过96%。

Abstract

Regioregular poly(3-hexylthiophene) (rr-P3HT) was synthesized by Heck reaction.The factors that influenced the molecular weight and regioregularity of P3HT were investigated

such as solvents

phase transfer catalysts

catalysts

reaction temperatures and reaction times.The molecular weight and regioregularity of rr-P3HT obtained were characterized with gel permeation chromatography (GPC) and magnetic nuclear resonance (NMR).The properties of rr-P3HT were characterized with ultraviolet absorption spectrum and photo-luminance spectrum.The results showed that rr-P3HT with Mn of 6700 and regioregularity over 96% was obtained by Heck reaction of 2-bromo-3-hexylthiophene when the mixture of DMF/THF(1∶1) was used as solvents

palladium acetate ［5%（mol） to monomer］ as a catalyst

tetrabutylamonium bromide ［100%（mol） to monomer］ as a phase transfer agent and potassium carbonate as a base at reaction temperature of 80℃ for 12 h.

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