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Polymers 2011, 3(1), 236-251; doi:10.3390/polym3010236
Article

Synthesis of Novel π-Conjugated Rod-Rod-Rod Triblock Copolymers Containing Poly(3-hexylthiophene) and Polyacetylene Segments by Combination of Quasi-Living GRIM and Living Anionic Polymerization

1,2,* , 3
,
4,5
 and
1
1 Department of Organic and Polymeric Materials, Graduate School of Science and Engineering, Tokyo Institute of Technology, 2-12-1-H-120, O-okayama, Meguro-Ku, Tokyo, 152-8552, Japan 2 PRESTO, Japan Science and Technology Agency (JST), 4-1-8, Honcho, Kawaguchi, Saitama 332-0012, Japan 3 Department of Organic Device Engineering, Yamagata University, Yonezawa, Yamagata, 992-8510 Japan 4 Department of Chemical Engineering, National Taiwan University, Taipei 106, Taiwan 5 Institute of Polymer Science and Engineering, National Taiwan University, Taipei 106, Taiwan
* Author to whom correspondence should be addressed.
Received: 17 November 2010 / Revised: 17 December 2010 / Accepted: 6 January 2011 / Published: 10 January 2011
(This article belongs to the Special Issue Conductive Polymers)
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Abstract

The first successful synthesis of a new rod-rod-rod triblock copolymer, polyacetylene(PA)-b-poly(3-hexylthiophene)(P3HT)-b-PA could be synthesized by a combination of quasi-living Grignard metathesis (GRIM) and living anionic polymerization. We first confirmed that poly(4-tolyl vinyl sulfoxide) (PTVS), which is a soluble precursor for PA, could be synthesized by living anionic polymerization in THF at −78 °C, initiated with 3-methyl-1,1-diphenylpentyllithium as the initiator in the presence of in situ-generated lithium enolate. The molecular weights (MWs) and polydispersities (PDIs) were well controlled (MW = 5,200–27,000, PDI = 1.10–1.22), respectively. A coil-rod-coil triblock copolymer, PTVS-b-P3HT-b-PTVS, (6,000-12,500-6,000) could also be synthesized, initiated with a P3HT-based difunctional macroinitiator in the presence of lithium enolate. GPC-RALLS and 1H NMR analyses confirmed a high degree of structural homogeneity of PTVS-b-P3HT-b-PTVS. A thermal transformation reaction of the polymer was carried out in the film state at 170 °C for 2 h to afford PA-b-P3HT-b-PA quantitatively, as monitored by TGA and FT-IR analyses. The optical and electronic properties as well as the morphological behavior of the block copolymers were investigated by UV-vis spectroscopy, conductivity measurement, and AFM observation.
Keywords: π-conjugated; poly(3-hexylthiophene); polyacetylene; GRIM polymerization; anionic polymerization π-conjugated; poly(3-hexylthiophene); polyacetylene; GRIM polymerization; anionic polymerization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Higashihara, T.; Liu, C.-L.; Chen, W.-C.; Ueda, M. Synthesis of Novel π-Conjugated Rod-Rod-Rod Triblock Copolymers Containing Poly(3-hexylthiophene) and Polyacetylene Segments by Combination of Quasi-Living GRIM and Living Anionic Polymerization. Polymers 2011, 3, 236-251.

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