Synthesis of a low-bandgap polymer bearing side groups containing phenoxy radicals

Journal of Materials Science volume 46, pages6556–6562(2011)Cite this article

Abstract

Poly(isothianaphthene methine) bearing di-tert-butylphenoxide in the side chain was prepared by reacting isothianaphthene and 3,5-di-tert-butyl-4-hydroxybenzaldehyde in the presence of POCl3. A reference polymer with no hydroxy group in the side chain was also synthesized. Both polymers are characterized by a low-bandgap with value of ca. 1.3 eV obtained by optical absorption spectroscopy, and ca. 1.7 eV estimated from an electrochemical method. After treatment with PbO2 as an oxidizer, phenoxy radicals were generated by oxidation in the polymer side groups. Optical absorption measurements and electron spin resonance (ESR) showed a characteristic signal due to phenoxy radicals. Magnetic properties of the polymer were examined with ESR and superconducting quantum interference device (SQUID) measurements. The results suggested that the polymer shows paramagnetic behavior.

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References

  1. 1.

    Rojo G, Agulló-López F, Campo J, Cano M, Lagunas M, Heras J (2001) Synth Met 124:201

    CAS  Article  Google Scholar 

  2. 2.

    Chen M, Perzon E, Robisson N, Jönsson S, Andersson M, Fahlman M, Berggren M (2004) Synth Met 146:233

    CAS  Article  Google Scholar 

  3. 3.

    Shi C, Wu Y, Zeng W, Xie Y, Yang K, Cao Y (2005) Macromol Chem Phys 206:1114

    CAS  Article  Google Scholar 

  4. 4.

    Xia J, Masaki N, Lira-Cantu M, Kim Y, Jiang K, Yanagida S (2008) J Am Chem Soc 130:1258

    CAS  Article  Google Scholar 

  5. 5.

    Hou J, Park M, Zhang S, Yao Y, Chen L, Li J, Yang Y (2008) Macromolecules 41:6012

    CAS  Article  Google Scholar 

  6. 6.

    Harpham M, Süzer Ö, Ma C, Bäuerle P, Goodson T (2009) J Am Chem Soc 131:973

    CAS  Article  Google Scholar 

  7. 7.

    Amrutha SR, Jayakannan M (2009) J Phys Chem B 113:5083

    CAS  Article  Google Scholar 

  8. 8.

    Kawabata K, Goto H (2010) Synth Met 160:2290

    CAS  Article  Google Scholar 

  9. 9.

    Rogojanu A, Rusu E, Dorohoi DO (2010) Int J Polym Anal Charact 15:210

    CAS  Article  Google Scholar 

  10. 10.

    Tarkuc S, Unver E, Udumb Y, Toppare L (2010) Eur Polym J 46:2199

    CAS  Article  Google Scholar 

  11. 11.

    Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger A (1985) J Chem Phys 82:5717

    CAS  Article  Google Scholar 

  12. 12.

    Quattrocchi C, Lazzaroni R, Brédas J, Kiebooms R, Vanderzande D, Gelan J, Meervelt L (1995) J Phys Chem 99:3932

    CAS  Article  Google Scholar 

  13. 13.

    Kiebooms R, Adriaensens P, Vanderzande D, Gelan J (1997) J Org Chem 62:1473

    CAS  Article  Google Scholar 

  14. 14.

    Meng H, Wudl F (2001) Macromolecules 34:1810

    CAS  Article  Google Scholar 

  15. 15.

    Kiebooms R, Goto H, Akagi K (2001) Synth Met 119:117

    CAS  Article  Google Scholar 

  16. 16.

    Kiebooms R, Goto H, Akagi K (2001) Macromolecules 34:7989

    CAS  Article  Google Scholar 

  17. 17.

    Liu C, Oshima K, Shimomura M, Miyauchi S (2005) J Appl Polym Sci 97:1848

    CAS  Article  Google Scholar 

  18. 18.

    Kim J, Qin Y, Stevens D, Kalihari V, Hillmyer M, Frisbie C (2009) J Phys Chem C 113:21928

    CAS  Article  Google Scholar 

  19. 19.

    Yamamoto T, Usui M, Ootsuka H, Iijima T, Fukumoto H, Sakai Y, Aramaki S, Yamamoto H, Yagi T, Tajima H, Okada T, Fukuda T, Emoto A, Ushijima H, Hasegawa M, Ohtsu H (2010) Macromol Chem Phys 211:2138

    CAS  Article  Google Scholar 

  20. 20.

    Xie C, Lahti P (1999) J Polym Sci A 37:779

    CAS  Article  Google Scholar 

  21. 21.

    Rajca A, Wongsriratanakul J, Rajca S, Cerny R (2004) Chem Eur J 10:3144

    CAS  Article  Google Scholar 

  22. 22.

    Vandeleene S, Jivanescu M, Stesmans A, Cuppens J, Bael M, Yamada H, Sato N, Verbiest T, Koeckelberghs G (2010) Macromolecules 43:2910

    CAS  Article  Google Scholar 

  23. 23.

    Goto H (2008) Polymer 49:3619

    CAS  Article  Google Scholar 

  24. 24.

    Kaneko T, Abe H, Namikoshi T, Marwanta E, Teraguchi M, Aoki T (2009) Synth Met 159:864

    CAS  Article  Google Scholar 

  25. 25.

    Nakahara K, Iriyama J, Iwasa S, Suguro M, Satoh M, Cairns E (2007) J Power Sources 163:1110

    CAS  Article  Google Scholar 

  26. 26.

    Ikeda H (2008) J Photopolym Sci Technol 21:327

    CAS  Article  Google Scholar 

  27. 27.

    Okuda Y, Lakshmikantham M, Cava M (1991) J Org Chem 56:6024

    CAS  Article  Google Scholar 

  28. 28.

    Goto H, Koyano T, Ikeda H, Yoshizaki R, Akagi K (2004) Polymer 45:4559

    CAS  Article  Google Scholar 

  29. 29.

    Faulques E, Wallnöfer W, Kuzmany H (1989) J Chem Phys 90:7585

    CAS  Article  Google Scholar 

  30. 30.

    Zerbi G, Magnoni MC, Hoogmartens I, Kiebooms R, Carleer R, Vanderzande D, Gelan J (1995) Adv Mater 7:1027

    CAS  Article  Google Scholar 

  31. 31.

    Neugebauer H, Kvarnström C, Brabec C, Sariciftci NS, Kiebooms R, Wudl F, Luzzati S (1999) J Chem Phys 110:12108

    CAS  Article  Google Scholar 

  32. 32.

    Yoshioka N, Nishide H, Tsuchida E (1990) Mol Cryst Liq Cryst 190:45

    CAS  Google Scholar 

  33. 33.

    Li Y, Cao Y, Gao J, Wang D, Yu G, Heeger A (1999) Synth Met 99:243

    CAS  Article  Google Scholar 

  34. 34.

    Bonardi L, Kanaan H, Camerel F, Jolinat P, Retailleau P, Ziessel R (2008) Adv Funct Mater 18:401

    CAS  Article  Google Scholar 

  35. 35.

    Scharber M, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger A, Brabec C (2006) Adv Mater 18:789

    CAS  Article  Google Scholar 

  36. 36.

    Nishide H, Doi R, Oyaizu K, Tsuchida E (2001) J Org Chem 66:1680

    CAS  Article  Google Scholar 

  37. 37.

    Chen W, Bowmaker G, Cooney R (2002) Phys Chem Chem Phys 4:4218

    CAS  Article  Google Scholar 

  38. 38.

    Yoshizawa K, Tanaka K, Yamabe T (1992) J Chem Phys 96:5516

    CAS  Article  Google Scholar 

Download references

Acknowledgements

We would like to thank the Chemical Analysis Division of Research Facility Center for Science and Technology, and the Glass Work Shop of the University of Tsukuba. We also thank Prof. Seiji Kojima (University of Tsukuba) for kindly providing Raman spectroscopy instrumentation.

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Affiliations

  1. Institute of Materials Science, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8573, Japan

    Yu Innami, Tamotsu Koyano, Satoshi Ohkawa, Kohsuke Kawabata, Masataka Kawamatsu, Kiyoto Matsuishi & Hiromasa Goto

  2. European Patent Office, Bayerstr 34, 80335, Munich, Germany

    Rafaёl H. L. Kiebooms

  3. Cryogenic Center, University of Tsukuba, Tsukuba, Ibaraki, 305-8577, Japan

    Tamotsu Koyano

  4. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki, 305-8571, Japan

    Masaaki Ichinohe

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  1. Yu Innami
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  2. Rafaёl H. L. Kiebooms
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  3. Tamotsu Koyano
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  4. Masaaki Ichinohe
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  5. Satoshi Ohkawa
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  6. Kohsuke Kawabata
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  7. Masataka Kawamatsu
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  8. Kiyoto Matsuishi
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  9. Hiromasa Goto
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Correspondence to Hiromasa Goto.

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Innami, Y., Kiebooms, R.H.L., Koyano, T. et al. Synthesis of a low-bandgap polymer bearing side groups containing phenoxy radicals. J Mater Sci 46, 6556–6562 (2011). https://doi.org/10.1007/s10853-011-5602-9

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Keywords

  • Electron Spin Resonance
  • Cyclic Voltammetry
  • Electron Spin Resonance Spectrum
  • High Occupied Molecular Orbital
  • Lower Unoccupied Molecular Orbital