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Liquid Crystalline Polythiophene Bearing Phenylnaphthalene Side-Chain

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† Institute of Materials Science, Graduate School of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
‡ Tsukuba Research Center for Interdisciplinary Materials Science, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
§ Central Research Laboratory, Technology & Development Division, Kanto Chemical Co., Inc., 1-7-1 Inari, Soka, Saitama 340-0003, Japan
∥ Division of Materials Science, Faculty of Pure and Applied Sciences, University of Tsukuba, 1-1-1 Tennodai, Tsukuba, Ibaraki 305-8573, Japan
*Fax: +81-29-853-4490. Telephone: +81-29-853-6905. E-mail: [email protected]
Cite this: Macromolecules 2012, 45, 4, 1825–1832
Publication Date (Web):February 9, 2012
https://doi.org/10.1021/ma202469g
Copyright © 2012 American Chemical Society
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Abstract

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Polythiophene bearing a 2-phenylnaphthalene side group at 3-position was synthesized from a 2,5-dibromothiophene monomer by two polymerization methods, i.e., Yamamoto dehalogenative polycondensation using Ni(cod)2 and Ni-catalyzed chain-growth polymerization. Polymers prepared by the former method had good solubility for organic solvents, 6300–8400 g mol–1 of number-average molecular weights, absorption bands at around 300 and 385 nm due to π–π* transitions at the phenylnaphthalene moiety and polythiophene backbone, a main fluorescence emission band at around 540 nm from the polythiophene backbone in solution and film state, and presence of enantiotropic liquid crystalline phases which enabled to construct an arrayed state. On the other hand, the latter polymer showed considerably red-shifted absorption and emission bands at around 444 and 585 nm in solution and 509 and 720 nm in film state respectively, but had poor solubility and unresolved mesophases.

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Synthetic procedures of compounds (1–6) and 1H NMR spectra of the polymers. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By

This article is cited by 20 publications.

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  9. Hiroto Kudo, Shuhei Matsubara, Hiroki Yamamoto, Takahiro Kozawa. Synthesis of hyperbranched polyacetals via a n  + b 2 -type polyaddition ( n  = 3, 8, 18, and 21): Candidate resists for extreme ultraviolet lithography. Journal of Polymer Science Part A: Polymer Chemistry 2015, 53 (20) , 2343-2350. https://doi.org/10.1002/pola.27686
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  11. Kosuke Shibasaki, Mari Watanabe, Masashi Kijima. Synthesis and characterization of soluble poly(3,4-phenylenedioxythiophene). Synthetic Metals 2015, 205 , 18-22. https://doi.org/10.1016/j.synthmet.2015.03.027
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  13. Jie Han, Zhuo-Zhi Wang, Jing Wu, Li-Rong Zhu. A room-temperature liquid crystalline polymer based on discotic 1,3,4-oxadizole. RSC Advances 2015, 5 (59) , 47579-47583. https://doi.org/10.1039/C5RA05983F
  14. Mari Watanabe, Masashi Kijima. Smectic-phase-induced interdigitated orientation of polythiophenes bearing phenylnaphthalene mesogen. Liquid Crystals 2014, 41 (7) , 897-907. https://doi.org/10.1080/02678292.2014.891766
  15. Mari Watanabe, Masashi Kijima. Solubility control of regioregular 3-substituted polythiophenes bearing 2-phenylnaphthalene side chain by copolymerisation. IOP Conference Series: Materials Science and Engineering 2014, 54 , 012023. https://doi.org/10.1088/1757-899X/54/1/012023
  16. Soundaram Jeevarathinam Ananthakrishnan, Prakash P. Wadgaonkar, Narayanasastri Somanathan. Linearly polarized emission from self-assembled microstructures of mesogenic polythiophenes. Phys. Chem. Chem. Phys. 2014, 16 (43) , 23809-23818. https://doi.org/10.1039/C4CP03457K
  17. Jianfeng Ban, Sheng Chen, Cheng Li, Xingzhu Wang, Hailiang Zhang. Influence of the spacer and molecular weight on the phase behavior of side-chain liquid crystalline polymers containing triphenylene discotic mesogen units as side groups. Polym. Chem. 2014, 5 (22) , 6558-6568. https://doi.org/10.1039/C4PY00788C
  18. Kai Yuan, Lie Chen, Yiwang Chen. Photovoltaic performance enhancement of P3HT/PCBM solar cells driven by incorporation of conjugated liquid crystalline rod-coil block copolymers. J. Mater. Chem. C 2014, 2 (19) , 3835-3845. https://doi.org/10.1039/C4TC00066H
  19. Noordini M. Salleh, Md. Rezaul Karim Sheikh, Rosiyah Yahya, Md. Rabiul Karim, Ahmad Danial Azzahari, Aziz Hassan. Effect of the lateral substituent on the mesomorphic behavior of side-chain liquid-crystalline polymers containing a Schiff base ester. Journal of Polymer Research 2013, 20 (12) https://doi.org/10.1007/s10965-013-0296-0
  20. Noordini M. Salleh, Md. Rezaul Karim Sheikh, Rosiyah Yahya, Md. Rabiul Karim, Aziz Hassan. Naphthalene group containing side chain liquid crystalline polymers and their rheological behavior. Journal of Polymer Research 2013, 20 (5) https://doi.org/10.1007/s10965-013-0131-7

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