ESR study of singlet oxygen generation and its behavior during the photo-oxidation of P3HT in solution

被引:44
作者
Chen, Liang [1 ]
Yamane, Shogo [1 ]
Mizukado, Junji [1 ]
Suzuki, Yasumasa [1 ]
Kutsuna, Shuzo [1 ]
Uchimaru, Tadafumi [1 ]
Suda, Hiroyuki [1 ]
机构
[1] Natl Inst Adv Ind Sci & Technol, Tsukuba, Ibaraki 3058565, Japan
关键词
POLYMER SOLAR-CELLS; MOLECULAR-OXYGEN; MASS-SPECTROMETRY; STATE; MECHANISMS; POLY(3-ALKYLTHIOPHENES); PHOTODEGRADATION; DEACTIVATION; DEGRADATION; INVOLVEMENT;
D O I
10.1016/j.cplett.2015.02.019
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
Generation of O-1(2) from poly-(3-hexylthiophene) (P3HT) irradiated in the presence of O-2 in chlorobenzene was investigated using ESR measurement, employing 2,2,6,6-tetramethylpiperidine (TEMP) as a spin trap. O-1(2) was found to be formed with O-center dot(2)- being produced in parallel at a branching ratio of 99:1. Additionally, the reaction of P3HT with O-1(2) was investigated using an endoperoxide as the O-1(2) source in CCl4 by MALDI-TOF MS measurement. The upper limit of the rate constant for the reaction of P3HT with O-1(2) was estimated using a kinetics simulation. These findings raise the understanding of the photo-oxidative degradation of P3HT. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:87 / 92
页数:6
相关论文
共 35 条
[1]
MECHANISMS OF PHOTODEGRADATION OF POLY(3-ALKYLTHIOPHENES) IN SOLUTION [J].
ABDOU, MSA ;
HOLDCROFT, S .
MACROMOLECULES, 1993, 26 (11) :2954-2962
[2]
Interaction of oxygen with conjugated polymers: Charge transfer complex formation with poly(3-alkylthiophenes) [J].
Abdou, MSA ;
Orfino, FP ;
Son, Y ;
Holdcroft, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) :4518-4524
[3]
ISOTOPE-DEPENDENT QUENCHING OF SINGLET MOLECULAR-OXYGEN (1-DELTA-G) BY GROUND-STATE OXYGEN IN SEVERAL PERHALOGENATED SOLVENTS [J].
AFSHARI, E ;
SCHMIDT, R .
CHEMICAL PHYSICS LETTERS, 1991, 184 (1-3) :128-132
[4]
Quantification of singlet oxygen from hematoporphyrin derivative by electron spin resonance [J].
Ando, T ;
Yoshikawa, T ;
Tanigawa, T ;
Kohno, M ;
Yoshida, N ;
Kondo, M .
LIFE SCIENCES, 1997, 61 (19) :1953-1959
[5]
THE SOLUBILITY OF OXYGEN AND OZONE IN LIQUIDS [J].
BATTINO, R ;
RETTICH, TR ;
TOMINAGA, T .
JOURNAL OF PHYSICAL AND CHEMICAL REFERENCE DATA, 1983, 12 (02) :163-178
[6]
Solution-processed organic solar cells [J].
Brabec, Christoph J. ;
Durrant, James R. .
MRS BULLETIN, 2008, 33 (07) :670-675
[7]
Practical quantitative biomedical applications of MALDI-TOF mass spectrometry [J].
Bucknall, M ;
Fung, KYC ;
Duncan, MW .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2002, 13 (09) :1015-1027
[8]
An ESR study on superoxide radical anion generation and its involvement in the photooxidative degradation of poly-3-hexylthiophene in chlorobenzene solution [J].
Chen, Liang ;
Mizukado, Junji ;
Suzuki, Yasumasa ;
Kutsuna, Shuzo ;
Aoyama, Yoshinori ;
Yoshida, Yuji ;
Suda, Hiroyuki .
CHEMICAL PHYSICS LETTERS, 2014, 605 :98-102
[9]
Mechanistic insight into TEMPO-inhibited polymerisation: simultaneous determination of oxygen and inhibitor concentrations by EPR [J].
Conte, Marco ;
Ma, Yun ;
Loyns, Colin ;
Price, Peter ;
Rippon, David ;
Chechik, Victor .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (13) :2685-2687
[10]
Frisch M.J., 2009, All calculations were performed with Gaussian 09