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

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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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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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Authors and 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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  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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  • DOI: https://doi.org/10.1007/s10853-011-5602-9

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