Photo-induced oxidation of polythiophene derivatives: Dependence on side chain structure

被引:24
作者
Aoyama, Yoshinori [1 ]
Yamanari, Toshihiro [2 ]
Koumura, Nagatoshi [2 ]
Tachikawa, Hiroto [3 ]
Nagai, Masaru [4 ]
Yoshida, Yuji [1 ,2 ]
机构
[1] Tokyo Inst Technol, Interdisciplinary Grad Sch Sci & Engn, Midori Ku, Yokohama, Kanagawa 2268503, Japan
[2] Natl Inst Adv Ind Sci & Technol, Res Ctr Photovolta Technol, Tsukuba, Ibaraki 3058565, Japan
[3] Hokkaido Univ, Fac Engn, Div Mat Chem, Kita Ku, Sapporo, Hokkaido 0608628, Japan
[4] Fuji Elect Adv Technol Co Ltd, Hino, Tokyo 1918502, Japan
关键词
Photooxidation; Poly(3-hexylthiophene); Side chain; Polymer solar cells; Fourier transform infrared spectroscopy; SOLAR-CELLS; PHOTOCHEMICAL STABILITY; CONJUGATED POLYMERS; EFFICIENCY; PHOTODEGRADATION; DEGRADATION; PARAMETERS; P3HT;
D O I
10.1016/j.polymdegradstab.2013.01.006
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The photooxidation of poly(3-hexylthiophene) (P3HT) has previously been investigated and it is known that the sulfur atom of the thiophene ring is oxidized into sulfur oxides by a hydroxyl radical that arises through hydrogen abstraction at the hexyl side chain at the alpha-position. In this study, in order to further investigate the photooxidation mechanism of the polymer, the side chain at alpha-position was varied and three different polythiophene derivatives with phenyl (P3PhT), tert-pentyl (P3DMPT), and alkoxy (P3OOT) groups were synthesized with no alpha-hydrogens. We observed the differences in the photochemical behavior of the polythiophene derivatives by UV-vis-NIR and FT-IR (ATR) spectroscopy during simulated solar light irradiation. It was found that the photooxidation of P3PhT and P3DMPT progressed in the same way as P3HT, whereas the analogous decomposition of P3OOT was not observed. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码:899 / 903
页数:5
相关论文
共 35 条
[21]   Influence of processing and intrinsic polymer parameters on photochemical stability of polythiophene thin films [J].
Madsen, Morten V. ;
Tromholt, Thomas ;
Bottiger, Arvid ;
Andreasen, Jens W. ;
Norrman, Kion ;
Krebs, Frederik C. .
POLYMER DEGRADATION AND STABILITY, 2012, 97 (11) :2412-2417
[22]   Thermo-cleavable polymers: Materials with enhanced photochemical stability [J].
Manceau, Matthieu ;
Helgesen, Martin ;
Krebs, Frederik C. .
POLYMER DEGRADATION AND STABILITY, 2010, 95 (12) :2666-2669
[23]   Effects of long-term UV-visible light irradiation in the absence of oxygen on P3HT and P3HT:PCBM blend [J].
Manceau, Matthieu ;
Chambon, Sylvain ;
Rivaton, Agnes ;
Gardette, Jean-Luc ;
Guillerez, Stephane ;
Lemaitre, Noella .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2010, 94 (10) :1572-1577
[24]   The mechanism of photo- and thermooxidation of poly(3-hexylthiophene) (P3HT) reconsidered [J].
Manceau, Matthieu ;
Rivaton, Agnes ;
Gardette, Jean-Luc ;
Guillerez, Stephane ;
Lemaitre, Noella .
POLYMER DEGRADATION AND STABILITY, 2009, 94 (06) :898-907
[25]   DESIGN, SYNTHESIS, AND CONTROL OF CONDUCTING POLYMER ARCHITECTURES - STRUCTURALLY HOMOGENEOUS POLY(3-ALKYLTHIOPHENES) [J].
MCCULLOUGH, RD ;
LOWE, RD ;
JAYARAMAN, M ;
ANDERSON, DL .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (04) :904-912
[26]  
McCullough RD, 1998, ADV MATER, V10, P93, DOI 10.1002/(SICI)1521-4095(199801)10:2<93::AID-ADMA93>3.3.CO
[27]  
2-6
[28]   Improving power conversion efficiency in polythiophene/fullerene-based bulk heterojunction solar cells [J].
Rait, Sukhbinder ;
Kashyap, Shipra ;
Bhatnagar, P. K. ;
Mathur, P. C. ;
Sengupta, S. K. ;
Kumar, J. .
SOLAR ENERGY MATERIALS AND SOLAR CELLS, 2007, 91 (09) :757-763
[29]   Light-induced degradation of the active layer of polymer-based solar cells [J].
Rivaton, Agnes ;
Chambon, Sylvain ;
Manceau, Matthieu ;
Gardette, Jean-Luc ;
Lamaitre, Noella ;
Guillerez, Stephane .
POLYMER DEGRADATION AND STABILITY, 2010, 95 (03) :278-284
[30]   CONJUGATED POLY(THIOPHENES) - SYNTHESIS, FUNCTIONALIZATION, AND APPLICATIONS [J].
RONCALI, J .
CHEMICAL REVIEWS, 1992, 92 (04) :711-738