Fulleropyrrolidines bearing π-conjugated moiety for polymer solar cells: Contribution of the chromophoric substituent on C60 to the photocurrent

ACS Applied Materials and Interfaces

Volumn 4, Issue 11, 2012, Pages 6133-6141

  Saravanan, Chinnusamy ^a   Liu, Che Liang ^a   Chang, Yi Min ^a   Lu, Jan De ^b   Hsieh, Yen Ju ^a   Rwei, Syang Peng ^b   Wang, Leeyih ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b NATIONAL TAIPEI UNIVERSITY OF TECHNOLOGY   (Taiwan)

Author keywords

C60; electron acceptor; fulleropyrrolidines; morphology; polymer solar cells; thermal stability

Indexed keywords

1 ,3-DIPOLARCYCLOADDITION; AZOMETHINE YLIDES; BULK HETEROJUNCTION SOLAR CELLS; C60; ELECTRON ACCEPTOR; ELECTRONIC COMMUNICATIONS; FULLEROPYRROLIDINES; HIGH TEMPERATURE AGING; INCIDENT PHOTON-TO-CURRENT EFFICIENCIES; PENDENT GROUPS; PHOTOACTIVE LAYERS; PHOTOEXCITED STATE; POLY-3-HEXYLTHIOPHENE; POLYMER SOLAR CELLS; POWER CONVERSION EFFICIENCIES; TERTHIOPHENES;

CONVERSION EFFICIENCY; CYCLIC VOLTAMMETRY; CYCLOADDITION; HETEROJUNCTIONS; MORPHOLOGY; SOLAR CELLS; THERMODYNAMIC STABILITY;

CONJUGATED POLYMERS;

FULLERENE C60; FULLERENE DERIVATIVE; ORGANOSELENIUM DERIVATIVE; POLY(3 HEXYL)SELENOPHENE; POLY(3-HEXYL)SELENOPHENE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; ELECTRON TRANSPORT; EQUIPMENT DESIGN; EQUIPMENT FAILURE; LIGHT; POWER SUPPLY; RADIATION EXPOSURE; SOLAR ENERGY;

ELECTRIC POWER SUPPLIES; ELECTRON TRANSPORT; EQUIPMENT DESIGN; EQUIPMENT FAILURE ANALYSIS; FULLERENES; LIGHT; ORGANOSELENIUM COMPOUNDS; PYRROLIDINES; SOLAR ENERGY;

EID: 84870527570     PISSN: 19448244     EISSN: 19448252     Source Type: Journal    
DOI: 10.1021/am301773t     Document Type: Article

References (63)

1. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324
2. Thompson, B. C.; Frechet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58
3. Brunetti, F. G.; Kumar, R.; Wudl, F. J. J. Mater. Chem. 2010, 20, 2934
4. Topham, P. D.; Parnell, A. J.; Hiorns, R. C. J. Polym. Sci., Part B: Polym. Phys. 2011, 49, 1131
5. Yu, G.; Gao, J.; Hummelen, J. C.; Wudl, F.; Heeger, A. J. Science 1995, 270, 1789
6. Brabec, C. J.; Sariciftci, N. S.; Hummelen, J. C. Adv. Funct. Mater. 2001, 11, 15
7. Singh, Th. B.; Marjanović, N.; Matt, G. J.; Günes, S.; Sariciftci, N. S.; Ramil, A. M.; Andreev, A.; Sitter, H.; Schwödiauer, R.; Bauer, S. Org. Electron. 2005, 6, 105
8. Chen, G.; Sasabe, H.; Wang, Z.; Wang, X.-F.; Hong, Z.; Yang, Y.; Kido, J. Adv. Mater. 2012, 24, 2768
9. Varotto, A.; Treat, N. D.; Jo, J.; Shuttle, C. G.; Batara, N. A.; Brunetti, F. G.; Seo, J. H.; Chabinyc, M. L.; Hawker, C. J.; Heeger, A. J.; Wudl, F. Angew. Chem., Int. Ed. 2011, 50, 5166
10. Chang, C.-Y.; Wu, C.-E.; Chen, S.-Y.; Cui, C.; Cheng, Y.-J.; Hsu, C.-S.; Wang, Y.-L.; Li, Y. Angew. Chem., Int. Ed. 2011, 50, 9386
11. Wei, Q.; Nishizawa, T.; Tajima, K.; Hashimoto, K. Adv. Mater. 2008, 20, 2211
12. He, Y.; Chen, H-Yu.; Hou, J.; Li, Y. J. Am. Chem. Soc. 2010, 132, 1377
13. Ross, R. B.; Cardona, C. M.; Guldi, D. M.; Sankaranarayanan, S. G.; Reese, M. O.; Kopidakis, N.; Peet, J.; Walker, B.; Bazan, G. C.; Keuren, E. V.; Holloway, B. C.; Drees, M. Nat. Matter 2009, 8, 208
14. Cheng, Y.-J.; Liao, M.-H.; Chang, C.-Y.; Kao, W.-S.; Wu, C.-E.; Hsu, C.-S. Chem. Mater. 2011, 23, 4056
15. Kim, K.-H.; Kang, H.; Nam, S. Y.; Jung, J.; Kim, P. S.; Cho, C.-H.; Lee, C.; Yoon, S. C.; Kim, B. J. Chem. Mater. 2011, 23, 5090
16. Zhang, Y.; Yip, H.-L.; Acton, O.; Hau, S. K.; Huang, F.; Jen, A. K.-Y. Chem. Mater. 2009, 21, 2598
17. Koster, L. J. A.; Mihailetchi, V. D.; Blom, P. W. M. Appl. Phys. Lett. 2006, 88, 093511
18. Cook, S.; Ohkita, H.; Kim, Y.; Benson-Smith, J. J.; Bradley, D. D. C.; Durrant, J. R. Chem. Phys. Lett. 2007, 445, 276
19. Nicolaidis, N. C.; Routley, B. S.; Holdsworth, J. L.; Belcher, W. J.; Zhou, X.; Dastoor, P. C. J. Phys. Chem. C 2011, 115, 7801
20. Beaujuge, P. M.; Amb, C. M.; Reynolds, J. R. Acc. Chem. Res. 2010, 43, 1396
21. Wu, J.-S.; Cheng, Y.-J.; Dubosc, M.; Hsieh, C.-H.; Chang, C.-Y.; Hsu, C.-S. Chem. Commun. 2010, 46, 3259
22. Ahmed, E.; Subramaniyan, S.; Kim, F. S.; Xin, H.; Jenekhe, S. A. Macromolecules 2011, 44, 7207
23. Peng, Q.; Liu, X.; Qin, Y.; Xu, J.; Li, M.; Dai, L. J. Mater. Chem. 2011, 21, 7714
24. Renz, J. A.; Keller, T.; Schneider, M.; Shokhovets, S.; Jandt, K. D.; Gobsch, G.; Hoppe, H. Sol. Energy Mater. Sol. Cells 2009, 93, 508
25. Wienk, M. M.; Kroon, J. M.; Verhees, W. J. H.; Knol, J.; Hummelen, J. C.; Van Hal, P. A.; Janssen, R. A. J. Angew. Chem., Int. Ed. 2003, 42, 3371
26. Chen, H.-Y.; Wu, J.-L.; Chen, C.-T.; Chen, C.-T. Chem. Commun. 2012, 48, 1012
27. Yamashiro, T.; Aso, Y.; Otsubo, T.; Tang, H.; Harima, Y.; Yamashita, K. Chem. Lett. 1999, 443
28. Fujitsuka, M.; Ito, O.; Yamashiro, T.; Aso, Y.; Otsubo, T. J. Phys. Chem. A 2000, 104, 4876
29. Fujitsuka, M.; Masuhara, A.; Kasai, H.; Oikawa, H.; Nakanishi, H.; Ito, O.; Yamashiro, T.; Aso, Y.; Otsubo, T. J. Phys. Chem. B 2001, 105, 9930
30. Chukharev, V.; Tkachenko, N. V.; Efimov, A.; Guldi, D. M.; Hirsch, A.; Scheloske, M.; Lemmetyinen, H. J. Phys. Chem. B 2004, 108, 16377
31. Bottari, G.; Olea, D.; Gómez-Navarro, C.; Zamora, F.; Gómez-Herrero, J.; Torres, T. Angew. Chem., Int. Ed. 2008, 47, 2026
32. Chamberlain, T. W.; Davies, E. S.; Khlobystov, A. N.; Champness, N. R. Chem.-Eur. J. 2011, 17, 3759
33. Wang, M.; Chesnut, E.; Sun, Y.; Tong, M.; Guide, M.; Zhang, Y.; Treat, N. D.; Varotto, A.; Mayer, A.; Chabinyc, M. L.; Nguyen, T.-Q.; Wudl, F. J. Phys. Chem. C 2012, 116, 1313
34. Schuster, D. I.; Li, K.; Guldi, D. M.; Palkar, A.; Echegoyen, L.; Stanisky, C.; Cross, R. J.; Niemi, M.; Tkachenko, N. V.; Lemmetyinen, H. J. Am. Chem. Soc. 2007, 129, 15973
35. Mikroyannidis, J. A.; Kabanakis, A. N.; Sharma, S. S.; Sharma, G. D. Adv. Funct. Mater. 2011, 21, 746
36. Mikroyannidis, J. A.; Tsagkournos, D. V.; Sharma, S. S.; Sharma, G. D. J. Phys. Chem. C 2011, 115, 7806
37. Sánchez, L.; Sierra, M.; Martín, N.; Guldi, D. M.; Wienk, M. W.; Janssen, R. A. J. Org. Lett. 2005, 7, 1691
38. Baffreau, J.; Dumur, F.; Hudhomme, P. Org. Lett. 2006, 8, 1307
39. Sandanayaka, A. S. D.; Taguri, Y.; Araki, Y.; Ishi-i, T.; Mataka, S.; Ito, O. J. Phys. Chem. B 2005, 109, 22502
40. Shirai, Y.; Zhao, Y.; Cheng, L.; Tour, J. M. Org. Lett. 2004, 6, 2129
41. Sánchez, L.; Herranz, M.; Martín, N. J. Mater. Chem. 2005, 15, 1409
42. Atienza, C.; Insuasty, B.; Seoane, C.; Martín, N.; Ramey, J.; Rahmand, G. M. A.; Guldi, D. M. J. Mater. Chem. 2005, 15, 124
43. Wang, C.-L.; Zhang, W.-B.; Van Horn, R. M.; Tu, Y.; Gong, X.; Cheng, S. Z. D.; Sun, Y.; Tong, M.; Seo, J.; Hsu, B. B. Y.; Heeger, A. J. Adv. Mater. 2011, 23, 2951
44. Sandanayaka, A. S. D.; Matsukawa, K.; Ishi-i, T.; Mataka, S.; Araki, Y.; Ito, O. J. Phys. Chem. B 2004, 108, 19995
45. Narutaki, M.; Takimiya, K.; Otsubo, T.; Harima, Y.; Zhang, H.; Araki, Y.; Ito, O. J. Org. Chem. 2006, 71, 1761
46. Al-Ibrahim, M.; Roth, H.-K.; Schroedner, M.; Konkin, A.; Zhokhavets, U.; Gobsch, G.; Scharff, P.; Sensfuss, S. Org. Electron. 2005, 6, 65
47. Darling, S. B. J. Phys. Chem. B 2008, 112, 8891
48. Darling, S. B.; Sternberg, M. J. Phys. Chem. B 2009, 113, 6215
49. Van Bavel, S. S.; Bärenklau, M.; De With, G.; Hoppe, H.; Loos, J. Adv. Funct. Mater. 2010, 20, 1458-1463
50. Kwon, M. H. Trans. Electr. Electron. Mater. 2012, 13, 98
51. Khlyabich, P. P.; Burkhart, B.; Thompson, B. C. J. Am. Chem. Soc. 2011, 133, 14534
52. Brabec, C. J.; Heeney, M.; McCulloch, I.; Nelson, J. Chem. Soc. Rev. 2011, 40, 1185
53. Thompson, B. C.; Fréchet, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58
54. Salim, T.; Wong, L. H.; Bräuer, B.; Kukreja, R.; Foo, Y. L.; Bao, Z.; Lam, Y. M. J. Mater. Chem. 2011, 21, 242
55. Jeong, S.; Kwon, Y.; Choi, B.-D.; Kwak, G.; Han, Y. S. Macromol. Chem. Phys. 2010, 211, 2474
56. Xin, H.; Guo, X.; Ren, G.; Watson, M. D.; Jenekhe, S. A. Adv. Energy Mater. 2012, 2, 575
57. Lee, J. K.; Ma, W. L.; Brabec, C. J.; Yuen, J.; Moon, J. S.; Kim, J. Y.; Lee, K.; Bazan, G. C.; Heeger, A. J. J. Am. Chem. Soc. 2008, 130, 3619
58. Peet, J.; Cho, N. S.; Lee, S. K.; Bazan, G. C. Macromolecules 2008, 41, 8655
59. Troshin, P. A.; Hoppe, H.; Renz, J.; Egginger, M.; Mayorova, J. Y.; Goryachev, A. E.; Peregudov, A. S.; Lyubovskaya, R. N.; Gobsch, G.; Sariciftci, N. S.; Razumov, V. F. Adv. Funct. Mater. 2009, 19, 779
60. Chen, W.; Nikiforov, M. P.; Darling, S. B. Energy Environ. Sci. 2012, 5, 8045
61. Liu, F.; Gu, Y.; Jung, J. W.; Jo, W. H.; Russell, T. P. J. Polym. Sci. Polym. Phys. 2012, 50, 1018
62. Meng, X.; Zhang, W.; Tan, Z.; Li, Y.; Ma, Y.; Wang, T.; Jiang, L.; Shu, C.; Wang, C. Adv. Funct. Mater. 2012, 22, 2187
63. Lai, Y.-C.; Higashihara, T.; Hsu, J.-C.; Ueda, M.; Chen, W.-C. Sol. Energy Mater. Sol. Cells 2012, 97, 164