journal article·2011-10

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

Yu Innami, Rafaёl H. L. Kiebooms, Tamotsu Koyano, Masaaki Ichinohe, Satoshi Ohkawa, Kohsuke Kawabata, Masataka Kawamatsu, Kiyoto Matsuishi, Hiromasa Goto

Journal of Materials Science· Volume 46· Issue 20
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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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Research context

OpenAlex topics: Conducting polymers and applications · Organic Electronics and Photovoltaics · Organic Light-Emitting Diodes Research

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References (38)

Show source-provided references
1. Rojo G, Agulló-López F, Campo J, Cano M, Lagunas M, Heras J (2001) Synth Met 124:20110.1016/S0379-6779(01)00446-5 ↗
2. Chen M, Perzon E, Robisson N, Jönsson S, Andersson M, Fahlman M, Berggren M (2004) Synth Met 146:23310.1016/j.synthmet.2004.08.002 ↗
3. Shi C, Wu Y, Zeng W, Xie Y, Yang K, Cao Y (2005) Macromol Chem Phys 206:111410.1002/macp.200500041 ↗
4. Xia J, Masaki N, Lira-Cantu M, Kim Y, Jiang K, Yanagida S (2008) J Am Chem Soc 130:125810.1021/ja075704o ↗
5. Hou J, Park M, Zhang S, Yao Y, Chen L, Li J, Yang Y (2008) Macromolecules 41:601210.1021/ma800820r ↗
6. Harpham M, Süzer Ö, Ma C, Bäuerle P, Goodson T (2009) J Am Chem Soc 131:97310.1021/ja803268s ↗
7. Amrutha SR, Jayakannan M (2009) J Phys Chem B 113:508310.1021/jp809994t ↗
8. Kawabata K, Goto H (2010) Synth Met 160:229010.1016/j.synthmet.2010.08.023 ↗
9. Rogojanu A, Rusu E, Dorohoi DO (2010) Int J Polym Anal Charact 15:21010.1080/10236661003743774 ↗
10. Tarkuc S, Unver E, Udumb Y, Toppare L (2010) Eur Polym J 46:219910.1016/j.eurpolymj.2010.08.002 ↗
11. Kobayashi M, Colaneri N, Boysel M, Wudl F, Heeger A (1985) J Chem Phys 82:571710.1063/1.448559 ↗
12. Quattrocchi C, Lazzaroni R, Brédas J, Kiebooms R, Vanderzande D, Gelan J, Meervelt L (1995) J Phys Chem 99:393210.1021/j100012a011 ↗
13. Kiebooms R, Adriaensens P, Vanderzande D, Gelan J (1997) J Org Chem 62:147310.1021/jo9604402 ↗
14. Meng H, Wudl F (2001) Macromolecules 34:181010.1021/ma001689v ↗
15. Kiebooms R, Goto H, Akagi K (2001) Synth Met 119:11710.1016/S0379-6779(00)01085-7 ↗
16. Kiebooms R, Goto H, Akagi K (2001) Macromolecules 34:798910.1021/ma001903f ↗
17. Liu C, Oshima K, Shimomura M, Miyauchi S (2005) J Appl Polym Sci 97:184810.1002/app.21976 ↗
18. Kim J, Qin Y, Stevens D, Kalihari V, Hillmyer M, Frisbie C (2009) J Phys Chem C 113:2192810.1021/jp9079926 ↗
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 211:213810.1002/macp.201000246 ↗
20. Xie C, Lahti P (1999) J Polym Sci A 37:77910.1002/(SICI)1099-0518(19990315)37:6<779::AID-POLA13>3.0.CO;2-2 ↗
21. Rajca A, Wongsriratanakul J, Rajca S, Cerny R (2004) Chem Eur J 10:314410.1002/chem.200306036 ↗
22. Vandeleene S, Jivanescu M, Stesmans A, Cuppens J, Bael M, Yamada H, Sato N, Verbiest T, Koeckelberghs G (2010) Macromolecules 43:291010.1021/ma100023g ↗
23. Goto H (2008) Polymer 49:361910.1016/j.polymer.2008.06.030 ↗
24. Kaneko T, Abe H, Namikoshi T, Marwanta E, Teraguchi M, Aoki T (2009) Synth Met 159:86410.1016/j.synthmet.2009.01.042 ↗
25. Nakahara K, Iriyama J, Iwasa S, Suguro M, Satoh M, Cairns E (2007) J Power Sources 163:111010.1016/j.jpowsour.2006.10.003 ↗
26. Ikeda H (2008) J Photopolym Sci Technol 21:32710.2494/photopolymer.21.327 ↗
27. Okuda Y, Lakshmikantham M, Cava M (1991) J Org Chem 56:602410.1021/jo00021a012 ↗
28. Goto H, Koyano T, Ikeda H, Yoshizaki R, Akagi K (2004) Polymer 45:455910.1016/j.polymer.2004.04.017 ↗
29. Faulques E, Wallnöfer W, Kuzmany H (1989) J Chem Phys 90:758510.1063/1.456192 ↗
30. Zerbi G, Magnoni MC, Hoogmartens I, Kiebooms R, Carleer R, Vanderzande D, Gelan J (1995) Adv Mater 7:102710.1002/adma.19950071213 ↗
31. Neugebauer H, Kvarnström C, Brabec C, Sariciftci NS, Kiebooms R, Wudl F, Luzzati S (1999) J Chem Phys 110:1210810.1063/1.479146 ↗
32. Yoshioka N, Nishide H, Tsuchida E (1990) Mol Cryst Liq Cryst 190:45
33. Li Y, Cao Y, Gao J, Wang D, Yu G, Heeger A (1999) Synth Met 99:24310.1016/S0379-6779(99)00007-7 ↗
34. Bonardi L, Kanaan H, Camerel F, Jolinat P, Retailleau P, Ziessel R (2008) Adv Funct Mater 18:40110.1002/adfm.200700697 ↗
35. Scharber M, Mühlbacher D, Koppe M, Denk P, Waldauf C, Heeger A, Brabec C (2006) Adv Mater 18:78910.1002/adma.200501717 ↗
36. Nishide H, Doi R, Oyaizu K, Tsuchida E (2001) J Org Chem 66:168010.1021/jo0013204 ↗
37. Chen W, Bowmaker G, Cooney R (2002) Phys Chem Chem Phys 4:421810.1039/b204557p ↗
38. Yoshizawa K, Tanaka K, Yamabe T (1992) J Chem Phys 96:551610.1063/1.462707 ↗