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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
Received: 17 November 2010; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(1):236-251.

Chicago/Turabian Style

Higashihara, Tomoya; Liu, Cheng-Liang; Chen, Wen-Chang; Ueda, Mitsuru. 2011. "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 3, no. 1: 236-251.


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