The mechanism of photo- and thermooxidation of poly(3-hexylthiophene) (P3HT) reconsidered

Polymer Degradation and Stability

Volumn 94, Issue 6, 2009, Pages 898-907

  Manceau, Matthieu ^a,b   Rivaton, Agnès ^a   Gardette, Jean Luc ^a   Guillerez, Stéphane ^b   Lemaître, Noëlla ^b  

^a CNRS   (France)

^b CEA GRENOBLE   (France)

Author keywords

Degradation; Infrared spectroscopy; Organic photovoltaic; Poly(3 hexylthiophene); UV visible light irradiation

Indexed keywords

AMBIENT ATMOSPHERES; DEGRADATION MECHANISMS; INFRARED SPECTRUM; MACROMOLECULAR BACKBONES; ORGANIC PHOTOVOLTAIC; ORGANIC SOLAR CELLS; OXIDATION PRODUCTS; POLY(3-HEXYLTHIOPHENE); RADICAL OXIDATIONS; SIDE-CHAINS; SINGLET OXYGENS; THERMAL AGEING; THERMAL STABILITIES; THIOPHENE RINGS; UV-VISIBLE LIGHT IRRADIATION;

CARRIER MOBILITY; CELL MEMBRANES; CHEMICAL MODIFICATION; DEGRADATION; IRRADIATION; OXYGEN; PHOTODEGRADATION; PHOTOVOLTAIC CELLS; SOLAR CELLS; SPECTROSCOPIC ANALYSIS; SPECTRUM ANALYSIS; THERMOOXIDATION; THIOPHENE;

INFRARED SPECTROSCOPY;

EID: 67349189966     PISSN: 01413910     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.polymdegradstab.2009.03.005     Document Type: Article

References (28)

1. Roncali J. Conjugated poly(thiophenes): synthesis, functionalization, and applications. Chem Rev 92 4 (1992) 711-738
2. McCullough R.D. The chemistry of conducting polythiophenes. Adv Mater 10 2 (1998) 93-116
3. Abdou M.S.A., and Holdcroft S. Solid-state photochemistry of π-conjugated poly(3-alkylthiophenes). Can J Chem 73 (1995) 1893-1901
4. Ljungqvist N., and Hjertberg T. Oxidative degradation of poly(3-octylthiophene). Macromolecules 28 18 (1995) 5993-5999
5. Caronna T., Forte M., Catellani M., and Meille S.V. Photodegradation and photostabilization studies of poly(3-butylthiophene) in the solid state. Chem Mater 9 4 (1997) 991-995
6. Chambon S., Rivaton A., Gardette J.-L., Firon M., and Lutsen L. Aging of a donor conjugated polymer: photochemical studies of the degradation of poly[2-methoxy-5-(3′,7′-dimethyloctyloxy)-1,4-phenylenevinyl ene]. J Polym Sci Part A Polym Chem 45 2 (2007) 317-331
7. 2 atmosphere: a powerful tool to elucidate the mechanism of UV-visible light oxidation of polymers - application to the photodegradation of MDMO-PPV. Polymer 49 15 (2008) 3288-3294
8. Chambon S., Rivaton A., Gardette J.-L., and Firon M. Durability of MDMO-PPV and MDMO-PPV: PCBM blends under illumination in the absence of oxygen. Sol Energy Mater Sol Cells 92 7 (2008) 785-792
9. Chambon S., Rivaton A., Gardette J.-L., and Firon M. Photo- and thermal degradation of MDMO-PPV:PCBM blends. Sol Energy Mater Sol Cells 91 5 (2007) 394-398
10. Holdcroft S. A photochemical study of poly(3-hexylthiophene). Macromolecules 24 17 (1991) 4834-4838
11. Abdou M.S.A., and Holdcroft S. Mechanisms of photodegradation of poly(3-alkylthiophenes) in solution. Macromolecules 26 11 (1993) 2954-2962
12. Skold C.N., and Schlessinger R.H. The reaction of singlet oxygen with a simple thiophene. Tetrahedron Lett 11 10 (1970) 791-794
13. Wasserman H.H., and Strehlow W. Reactions of singlet oxygen with thiophenes. Tetrahedron Lett 11 10 (1970) 795-796
14. Manceau M., Rivaton A., and Gardette J.-L. Involvement of singlet oxygen in the solid-state photochemistry of P3HT. Macromol Rapid Commun 29 22 (2008) 1823-1827
15. Lemaire J., Arnaud R., and Gardette J.-L. Rev Gen Caout Plast 613 (1981) 87-92
16. Carlsson D.J., Brousseau R., Zhang C., and Wiles D.M. Identification of products from polyolefin oxidation by derivatization reactions (1988), American Chemical Society, Anheim 376-389 ACS Symposium Series, Anheim, 1988; Society AC
17. Wilhelm C., and Gardette J.-L. Infrared identification of carboxylic acids formed in polymer photooxidation. J Appl Polym Sci 51 8 (1994) 1411-1420
18. March J. Advanced organic chemistry. 2Rev ed. (1977), McGraw-Hill Education, New York p. 1440
19. Brown P.J., Thomas D.S., Köhler A., Wilson J.S., Kim J.-S., Ramsdale C.M., et al. Effect of interchain interactions on the absorption and emission of poly(3-hexylthiophene). Phys Rev B Condens Matter 67 (2003) 064203
20. Chen T.-A., Wu X., and Rieke R.D. Regiocontrolled synthesis of poly(3-alkylthiophenes) mediated by Rieke zinc: their characterization and solid-state properties. J Am Chem Soc 117 1 (1995) 233-244
21. Socrates G. Infrared and Raman characteristic group frequencies. 3rd ed. (2001), John Wiley & Sons Ltd, Chichester
22. Gardette J.-L. Fundamental and technical aspects of the photooxidation of polymers. In: Halim Hamid S. (Ed). Handbook of polymer degradation. 2nd ed. vol. 1 (2000), Marcel Dekker, Inc., New York 671-698
23. Rivaton A., and Gardette J.-L. Photodegradation of polyethersulfone and polysulfone. Polym Degrad Stab 66 3 (1999) 385-403
24. SDBSWeb, National Institute of Advanced Industrial Science and Technology, http://riodb01.ibase.aist.go.jp/sdbs/.
25. Berkowitz J., Ellison G.B., and Gutman D. Three methods to measure RH bond energies. J Phys Chem 98 11 (1994) 2744-2765
26. Jouan X., and Gardette J.-L. Photooxidation of ABS of long-wavelengths. J Polym Sci Part A Polym Chem 29 5 (1991) 685-696
27. Piton M., and Rivaton A. Photooxidation of polybutadiene at long-wavelengths (λ > 300 nm). Polym Degrad Stab 53 3 (1996) 343-359
28. Barnes I., Hjorth J., and Mihalopoulos N. Dimethyl sulfide and dimethyl sulfoxide and their oxidation in the atmosphere. Chem Rev 106 3 (2006) 940-975