Crystalline random conjugated copolymers with multiple side chains: Tunable intermolecular interactions and enhanced charge transport and photovoltaic properties

Macromolecules

Volumn 43, Issue 7, 2010, Pages 3306-3313

  Wu, Pei Tzu ^a   Ren, Guoqiang ^a   Jenekhe, Samson A ^a,b  

^a University of Washington   (United States)

^b UNIVERSITY OF WASHINGTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BULK HETEROJUNCTION; BULK HETEROJUNCTION SOLAR CELLS; CHARGE TRANSPORT; CONJUGATED COPOLYMERS; COPOLYMER COMPOSITIONS; CRYSTALLINE PACKING; HOMOPOLYMERS; INTERMOLECULAR INTERACTIONS; LAMELLAR CRYSTALLINE STRUCTURES; NANO SCALE; OPTOELECTRONIC PROPERTIES; PHASE SEPARATED MORPHOLOGY; PHOTOVOLTAIC PROPERTY; POLY(3-BUTYLTHIOPHENE); POWER CONVERSION EFFICIENCIES; RANDOM COPOLYMER; RANDOM COPOLYMERIZATION; RECRYSTALLIZATIONS; SIDE CHAINS; SIDE-CHAIN; SPACE CHARGE LIMITED CURRENTS; STACKING DISTANCES; TRANSMISSION ELECTRON MICROSCOPY IMAGES;

CONJUGATED POLYMERS; CONVERSION EFFICIENCY; COPOLYMERIZATION; COPOLYMERS; CRYSTALLINE MATERIALS; FULLERENES; LAMELLAR STRUCTURES; LITHIUM BATTERIES; ORGANIC POLYMERS; PLASTIC PRODUCTS; SCANNING ELECTRON MICROSCOPY; SOLAR CELLS; TRANSMISSION ELECTRON MICROSCOPY; X RAY DIFFRACTION;

HETEROJUNCTIONS;

EID: 77951572407     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma100006x     Document Type: Article

References (59)

1. (a) Chen, T.-A.; Wu, X.; Rieke, R. D. J. Am. Chem. Soc. 1995, 117, 233-244.
2. (b) Osaka, I.; McCullough, R. D. Acc. Chem. Res. 2008, 41, 1202-1214.
3. Berresheim, A. J.; Müller, M.; Müllen, K. Chem. Rev. 1999, 99, 1747-1785.
4. Suzuki, Y.; Hashimoto, K.; Tajima, K. Macromolecules 2007, 40, 6521-6528.
5. (a)Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644.
6. (b) Egbe, D. A. M.; Carbonnier, B.; Birckner, E.; Grummt, U.-W. Prog. Polym. Sci. 2009, 34, 1023-1067.
7. Rüuhe, J.;Ezquerra, T. A.;Wegner, G. Synth.Met. 1989, 28, 177-181.
8. (a) Scherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477-487.
9. (b)Neher, D. Macromol. Rapid Commun. 2001, 22, 1365-1385.
10. (c) Leclerc, M. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 2867-2873.
11. Blouin, N.; Leclerc, M. Acc. Chem. Res. 2008, 41, 1110-1119.
12. (a) Zhu, Y.; Alam, M. M.; Jenekhe, S. A. Macromolecules 2002, 35, 9844-9846.
13. (b) Zhu, Y.; Alam, M. M.; Jenekhe, S. A. Macromolecules 2003, 36, 8958-8968.
14. (a) Kanbara, T.; Yamamoto, T. Macromolecules 1993, 26, 3464-3466.
15. (b) Yamamoto, T.; Zhou, Z.-h.; Kanbara, T.; Shimura, M.; Kizu, K.; Maruyama, T.; Nakamura, Y.; Fukuda, T.; Lee, Bang-L.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K.; Sasaki, S. J. Am. Chem. Soc. 1996, 118, 10389-10399.
16. (c) Cui, Y.; Zhang, X.; Jenekhe, S. A. Macromolecules 1999, 32, 3824-3826.
17. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
18. Grimsdale, A. C.; Leok Chan, K.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897-1091.
19. (a) Yap, B. K.; Xia, R.; Campoy-Quiles, M.; Stavrinou, P. N.; Bradley, D. D. C. Nat. Mater. 2008, 7, 376-380.
20. (b) Jenekhe, S. A. Nat. Mater. 2008, 7, 354-355.
21. (a) Wu, P.-T.; Xin, H.; Kim, F. S.; Ren, G.; Jenekhe, S. A. Macromolecules 2009, 42, 8817-8826.
22. (b) Babel, A.; Jenekhe, S. A. Synth. Met. 2005, 148, 169-173.
23. (c) Samitsu, S.; Shimomura, T.; Heike, S.; Hashizume, T.; Ito, K. Macromolecules 2008, 41, 8000-8010.
24. (d) Causin,V.; Marega, C.; Marigo, A.; Valentini, L.; Kenny, J. M. Macromolecules 2005, 38, 409-415.
25. (e) Pal, S.; Roy, S.; Nandi, A. K. J. Phys. Chem. B 2005, 109, 18332-18341.
26. (a) Mena-Osteriz, E.; Meyer, A.; Langeveld-Voss, B. M. W.; Janssen, R. A. J.; Meijer, E. W.; Bäuerle, P. Angew. Chem., Int. Ed. 2000, 39, 2679-2684.
27. (b) Brinkmann, M.; Rannou, P. Macromolecules 2009, 42, 1125-1130.
28. (a) Ong, B. S.; Wu, Y.; Liu, P.; Gardner, S. J. Am. Chem. Soc. 2004, 126, 3378-3379.
29. (b) Ong, B. S.;Wu,Y.; Li,Y.; Liu, P.; Pan, H. Chem.-Eur. J. 2008, 14, 4766-4778.
30. McCulloch, I.; Heeney, M.; Bailey, C.; Genevicius, K.; MacDonald, I.; Shkunov, M.; Sparrowe, D.; Tierney, S.; Wagner, R.; Zhang, W.; Chabinyc, M. L.; Kline, R. J.; McGehee, M. D.; Toney, M. F. Nat. Mater. 2006, 5, 328-333.
31. Kline, R. J.; DeLongchamp, D. M.; Fischer, D. A.; Lin, E. K.; Richter, L. J.; Chabinyc, M. L.; Toney, M. F.; Heeney, M.; McCulloch, I. Macromolecules 2007, 40, 7960-7965.
32. Osaka, I.; Zhang, R.; Sauvé, G.; Smilgies, D.-M.; Kowalewski, T.; McCullough, R. D. J. Am. Chem. Soc. 2009, 131, 2521-2529.
33. Ahmed, E.; Kim, F. S.; Xin, H.; Jenekhe, S. A. Macromolecules 2009, 42, 8615-8618.
34. (a) Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D. Macromolecules 2005, 38, 8649-8656.
35. (b) Wu, P.-T.; Ren, G.; Li, C.; Mezzenga, R.; Jenekhe, S. A. Macromolecules 2009, 42, 2317-2320.
36. (c) Ren, G.; Wu, P.-T.; Jenekhe, S. A. Chem. Mater. 2010, 22, 2020-2026.
37. (a) Lowe, R. S.; Khersonsky, S. M.; McCullough, R. D. Adv. Mater. 1999, 11, 250-253.
38. (b) Heeny, M.; Zhang, W.; Duffy, W.; McCulloch, I.; Koller, G. World Patent Application WO2007/059838, 2007.
39. Xin, H.; Guo, X.; Kim, F. S.; Ren, G.; Watson, M. D.; Jenekhe, S. A. J. Mater. Chem. 2009, 19, 5303-5310.
40. (a) Murgatroyd, P. N. J. Phys. D: Appl. Phys. 1970, 3, 151-156.
41. (b) Mihailetchi, V. D.; Xie, H.; de Boer, B.; Koster, L. J. A.; Blom, P. W. M. Adv. Funct. Mater. 2006, 16, 699-708.
42. (a) Lu, X.; Windle, A. H. Polymer 1995, 36, 451-459.
43. (b) Stagnaro, P.; Boragno, L.; Canetti, M.; Forlini, F.; Azzurri, F.; Alfonso, G. C. Polymer 2009, 50, 5242-5249.
44. (a) Patterson, A. L. Phys. Rev. 1939, 56, 978-982.
45. (b) Motaung, D. E.; Malgas, G. F.; Arendse, C. J.; Mavundla, S. E.; Oliphant, C. J.; Knoesen, D. J. Mater. Sci. 2009, 44, 3192-3197.
46. Pal, S.; Nandi, A. K. Macromolecules 2003, 36, 8426-8432.
47. (a) Nguyen, L. H.; Hoppe, H.; Erb, T.; Günes, S.; Gobsch, G.; Sariciftci, N. S. Adv. Funct. Mater. 2007, 17, 1071-1078.
48. (b) Hiorns, R. C.; de Bettignies, R.; Leroy, J.; Bailly, S.; Firon, M.; Sentein, C.; Khoukh, A.; Preud'homme, H.; Dagron-Lartigau, C. Adv. Funct. Mater. 2006, 16, 2263-2273.
49. (a) Xin, H.; Kim, F. S.; Jenekhe, S. A. J. Am. Chem. Soc. 2008, 130, 5424-5425.
50. (b) Xin, H.; Ren, G.; Kim, F. S.; Jenekhe, S. A. Chem. Mater. 2008, 20, 6199-6207.
51. Gadisa, A.; Oosterbaan, W. D.; Vandewal, K.; Bolsée, J.-C.; Bertho, S.; D'Haen, J.; Lutsen, L.; Vanderzande, D.; Manca, J. V. Adv. Funct. Mater. 2009, 19, 3300-3306.
52. (a) Jackson, T.; Wang, J. U.S. Patent 6,621,098, 2003.
53. (b) Wang, J.; Gundlach, D. J.; Benesi, A. J.; Jackson, T. N. Abstract, 1999 Electronic Materials Conf., Santa Barbara, CA, June 30-July 2, 1999.
54. (c) Zen, A.; Saphiannikova, M.; Neher, D.; Asawapirom, U.; Scherf, U. Chem. Mater. 2005, 17, 781-786.
55. (d) Thompson, B. C.; Kim, B. J.; Kavulak, D. F.; Sivula, K.; Mauldin, C.; Fréchet, J. M. J. Macromolecules 2007, 40, 7425-7428.
56. Moulé, A. J.; Allard, S.; Kronenberg, N. M.; Tsami, A.; Scherf, U.; Meerholz, K. J. Phys. Chem. C 2008, 112, 12583-12589.
57. Mayer, A. C.; Toney, M. F.; Scully, S. R.; Rivnay, J.; Brabec, C. J.; Scharber, M.; Koppe, M.; Heeney, M.; McCulloch, I.; McGehee, M. D. Adv. Funct. Mater. 2009, 19, 1173-1179.
58. (a) Jenekhe, S. A.; Osaheni, J. A. Science 1994, 265, 765-768.
59. (b) Jenekhe, S. A. Adv. Mater. 1995, 7, 309-311.