Semiconducting nanowires from hairpin-shaped self-assembling sexithiophenes

Journal of Physical Chemistry B

Volumn 114, Issue 45, 2010, Pages 14778-14786

  Tsai, Wei Wen ^a   Tevis, Ian D ^a   Tayi, Alok S ^b   Cui, Honggang ^b   Stupp, Samuel I ^a,b,c,d  

^a NORTHWESTERN UNIVERSITY   (United States)

^b Northwestern University   (United States)

^c Department of Medicine ^*  (United States)

^d International Institute for Nanotechnology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; ENERGY HARVESTING; FIELD EFFECT TRANSISTORS; HYDROGEN; HYDROGEN BONDS; MOLECULES; NANOWIRES; ORGANIC SOLVENTS; SELF ASSEMBLY; SEMICONDUCTING FILMS; SPECTROSCOPIC ANALYSIS; TOLUENE;

ABSORBANCES; AMIDE GROUPS; CHARGE TRANSPORT; CONJUGATED ORGANIC MOLECULES; ENERGY APPLICATIONS; HYDROGEN BONDINGS; J AGGREGATES; LIGHT-HARVESTING; NMR ANALYSIS; NONPOLAR ORGANIC SOLVENTS; ORDERED STACKING; ORGANOGELS; P-TYPE; SELF-ASSEMBLE; SELF-ASSEMBLING; SEMICONDUCTING BEHAVIOR; SEMICONDUCTING NANOWIRES; SEXITHIOPHENES; SPECTROSCOPIC MEASUREMENTS; UNIFORM DIAMETER; UV-VIS SPECTRUM;

SYNTHESIS (CHEMICAL);

EID: 78650134585     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp105227p     Document Type: Article

References (91)

1. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; Dos Santos, D. A.; Bredas, J. L.; Logdlund, M.; Salaneck, W. R. Nature 1999, 397, 121-128.
2. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590.
3. Peet, J.; Heeger, A. J.; Bazan, G. C. Acc. Chem. Res. 2009, 42, 1700-1708.
4. Katz, H. E.; Bao, Z. N.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359-369.
5. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070-4098.
6. Murphy, A. R.; Frechet, J. M. J. Chem. Rev. 2007, 107, 1066-1096.
7. Kelley, T. W.; Muyres, D. V.; Baude, P. F.; Smith, T. P.; Jones, T. D. Mater. Res. Soc. Symp. Proc. 2003, 771, 169-179.
8. Podzorov, V.; Sysoev, S. E.; Loginova, E.; Pudalov, V. M.; Gershenson, M. E. Appl. Phys. Lett. 2003, 83, 3504-3506.
9. Sofos, M.; Goldberger, J.; Stone, D. A.; Allen, J. E.; Ma, Q.; Herman, D. J.; Tsai, W. W.; Lauhon, L. J.; Stupp, S. I. Nat. Mater. 2009, 8, 68-75.
10. Tang, M. L.; Reichardt, A. D.; Miyaki, N.; Stoltenberg, R. M.; Bao, Z. J. Am. Chem. Soc. 2008, 130, 6064-6065.
11. Zaumseil, J.; Sirringhaus, H. Chem. Rev. 2007, 107, 1296-1323.
12. Cho, S. N.; Yuen, J.; Kim, J. Y.; Lee, K.; Heeger, A. J. Appl. Phys. Lett. 2006, 89, 153505.
13. Tantiwiwat, M.; Tamayo, A.; Luu, N.; Dang, X. D.; Nguyen, T. Q. J. Phys. Chem. C 2008, 112, 17402-17407.
14. Li, W. S.; Yamamoto, Y.; Fukushima, T.; Saeki, A.; Seki, S.; Tagawa, S.; Masunaga, H.; Sasaki, S.; Takata, M.; Aida, T. J. Am. Chem. Soc. 2008, 130, 8886-8887.
15. Nakamura, T.; Kanato, H.; Araki, Y.; Ito, O.; Takimiya, K.; Otsubo, T.; Aso, Y. J. Phys. Chem. A 2006, 110, 3471-3479.
16. Yang, C.; Lee, J. K.; Heeger, A. J.; Wudl, F. J. Mater. Chem. 2009, 19, 5416-5423.
17. Bullock, J. E.; Carmieli, R.; Mickley, S. M.; Vura-Weis, J.; Wasielewski, M. R. J. Am. Chem. Soc. 2009, 131, 11919-11929.
18. Forrest, S. R. Nature 2004, 428, 911-918.
19. Anderson, P. W. Phys. Rev. 1958, 109, 1492-1505.
20. Coropceanu, V.; Cornil, J.; da Silva, D. A.; Olivier, Y.; Silbey, R.; Bredas, J. L. Chem. Rev. 2007, 107, 926-952.
21. Sundar, V. C.; Zaumseil, J.; Podzorov, V.; Menard, E.; Willett, R. L.; Someya, T.; Gershenson, M. E.; Rogers, J. A. Science 2004, 303, 1644-1646.
22. Podzorov, V.; Menard, E.; Borissov, A.; Kiryukhin, V.; Rogers, J. A.; Gershenson, M. E. Phys. Rev. Lett. 2004, 93, 086602.
23. Zeis, R.; Besnard, C.; Siegrist, T.; Schlockermann, C.; Chi, X. L.; Kloc, C. Chem. Mater. 2006, 18, 244-248.
24. Lee, J. Y.; Roth, S.; Park, Y. W. Appl. Phys. Lett. 2006, 88, 252106.
25. Sirringhaus, H.; Brown, P. J.; Friend, R. H.; Nielsen, M. M.; Bechgaard, K.; Langeveld-Voss, B. M. W.; Spiering, A. J. H.; Janssen, R. A. J.; Meijer, E. W.; Herwig, P.; de Leeuw, D. M. Nature 1999, 401, 685-688.
26. Moon, H.; Zeis, R.; Borkent, E. J.; Besnard, C.; Lovinger, A. J.; Siegrist, T.; Kloc, C.; Bao, Z. N. J. Am. Chem. Soc. 2004, 126, 15322-15323.
27. Mas-Torrent, M.; Hadley, P.; Bromley, S. T.; Ribas, X.; Tarres, J.; Mas, M.; Molins, E.; Veciana, J.; Rovira, C. J. Am. Chem. Soc. 2004, 126, 8546-8553.
28. Lan, Y. K.; Huang, C. I. J. Phys. Chem. B 2009, 113, 14555-14564.
29. Stone, D. A.; Hsu, L.; Stupp, S. I. Soft Matter 2009, 5, 1990-1993.
30. Messmore, B. W.; Hulvat, J. F.; Sone, E. D.; Stupp, S. I. J. Am. Chem. Soc. 2004, 126, 14452-14458.
31. Hill, J. P.; Jin, W. S.; Kosaka, A.; Fukushima, T.; Ichihara, H.; Shimomura, T.; Ito, K.; Hashizume, T.; Ishii, N.; Aida, T. Science 2004, 304, 1481-1483.
32. Hoeben, F. J. M.; Jonkheijm, P.; Meijer, E. W.; Schenning, A. P. H. J. Chem. Rev. 2005, 105, 1491-1546.
33. Ajayaghosh, A.; Praveen, V. K. Acc. Chem. Res. 2007, 40, 644-656.
34. Ryu, J. H.; Hong, D. J.; Lee, M. Chem. Commun. 2008, 1043-1054.
35. Sugiyasu, K.; Fujita, N.; Shinkai, S. Angew. Chem., Int. Ed. 2004, 43, 1229-1233.
36. Kawano, S.; Fujita, N.; Shinkai, S. Chem.sEur. J. 2005, 11, 4735-4742.
37. Kaiser, T. E.; Wang, H.; Stepanenko, V.; Wurthner, F. Angew. Chem., Int. Ed. 2007, 46, 5541-5544.
38. Ghosh, S.; Li, X. Q.; Stepanenko, V.; Wurthner, F. Chem. - Eur. J. 2008, 14, 11343-11357.
39. Schillinger, E. K.; Mena-Osteritz, E.; Hentschel, J.; Borner, H. G.; Bauerle, P. Adv. Mater. 2009, 21, 1562-1567.
40. Palmer, L. C.; Stupp, S. I. Acc. Chem. Res. 2008, 41, 1674-1684.
41. Hartgerink, J. D.; Zubarev, E. R.; Stupp, S. I. Curr. Opin. Solid State Mater. Sci. 2001, 5, 355-361.
42. Schenning, A. P. H. J.; Meijer, E. W. Chem. Commun. 2005, 3245-3258.
43. Schoonbeek, F. S.; van Esch, J. H.; Wegewijs, B.; Rep, D. B. A.; de Haas, M. P.; Klapwijk, T. M.; Kellogg, R. M.; Feringa, B. L. Angew. Chem., Int. Ed. 1999, 38, 1393-1397.
44. Yagai, S.; Kinoshita, T.; Kikkawa, Y.; Karatsu, T.; Kitamura, A.; Honsho, Y.; Seki, S. Chem.sEur. J. 2009, 15, 9320-9324.
45. Mishra, A.; Ma, C. Q.; Bauerle, P. Chem. ReV. 2009, 109, 1141-1276.
46. Katz, H. E.; Lovinger, A. J.; Laquindanum, J. G. Chem. Mater. 1998, 10, 457.
47. Dimitrakopoulos, C. D.; Furman, B. K.; Graham, T.; Hegde, S.; Purushothaman, S. Synth. Met. 1998, 92, 47-52.
48. Katz, H. E.; Lovinger, A. J.; Johnson, J.; Kloc, C.; Siegrist, T.; Li, W.; Lin, Y. Y.; Dodabalapur, A. Nature 2000, 404, 478-481.
49. Facchetti, A.; Mushrush, M.; Yoon, M. H.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13859-13874.
50. Hanabusa, K.; Yamada, M.; Kimura, M.; Shirai, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1949-1951.
51. de Loos, M.; van Esch, J.; Stokroos, I.; Kellogg, R. M.; Feringa, B. L. J. Am. Chem. Soc. 1997, 119, 12675-12676.
52. van Bommel, K. J. C.; van der Pol, C.; Muizebelt, I.; Friggeri, A.; Heeres, A.; Meetsma, A.; Feringa, B. L.; van Esch, J. Angew. Chem., Int. Ed. 2004, 43, 1663-1667.
53. Hanessian, S.; Vinci, V.; Fettis, K.; Maris, T.; Viet, M. T. P. J. Org. Chem. 2008, 73, 1181-1191.
54. Friggeri, A.; van der pol, C.; van Bommel, K. J. C.; Heeres, A.; Stuart, M. C. A.; Feringa, B. L.; van Esch, J. Chem. - Eur. J. 2005, 11, 5353-5361.
55. Zweep, N.; Hopkinson, A.; Meetsma, A.; Browne, W. R.; Feringa, B. L.; van Esch, J. H. Langmuir 2009, 25, 8802-8809.
56. Kobayashi, S.; Hanabusa, K.; Hamasaki, N.; Kimura, M.; Shirai, H.; Shinkai, S. Chem. Mater. 2000, 12, 1523-1525.
57. Kobayashi, S.; Hamasaki, N.; Suzuki, M.; Kimura, M.; Shirai, H.; Hanabusa, K. J. Am. Chem. Soc. 2002, 124, 6550-6551.
58. Kato, T.; Kondo, G.; Hanabusa, K. Chem. Lett. 1998, 193-194.
59. Kimura, M.; Kitamura, T.; Muto, T.; Hanabusa, K.; Shirai, H.; Kobayashi, N. Chem. Lett. 2000, 1088-1089.
60. Diaz, D. D.; Cid, J. J.; Vazquez, P.; Torres, T. Chem. - Eur. J. 2008, 14, 9261-9273.
61. Albano, V. G.; Bandini, M.; Barbarella, G.; Melucci, M.; Monari, M.; Piccinelli, F.; Tommasi, S.; Umani-Ronchi, A. Chem. - Eur. J. 2006, 12, 667-675.
62. Melucci, M.; Barbarella, G.; Gazzano, M.; Cavallini, M.; Biscarini, F.; Bongini, A.; Piccinelli, F.; Monari, M.; Bandini, M.; Umani-Ronchi, A.; Biscarini, P. Chem. - Eur. J. 2006, 12, 7304-7312.
63. Perez, E. M.; Martin, N. Pure Appl. Chem. 2010, 82, 523-533.
64. Curtis, M. D.; Cao, J.; Kampf, J. W. J. Am. Chem. Soc. 2004, 126, 4318-4328.
65. Takahashi, M.; Masui, K.; Sekiguchi, H.; Kobayashi, N.; Mori, A.; Funahashi, M.; Tamaoki, N. J. Am. Chem. Soc. 2006, 128, 10930-10933.
66. Zhu, S. S.; Swager, T. M. J. Am. Chem. Soc. 1997, 119, 12568-12577.
67. Sayar, M.; Stupp, S. I. Phys. Rev. E 2005, 72, 011803.
68. Tsai, W. W.; Li, L. S.; Cui, H. G.; Jiang, H. Z.; Stupp, S. I. Tetrahedron 2008, 64, 8504-8514.
69. Pons, M.; Millet, O. Prog. Nucl. Magn. Reson. Spectrosc. 2001, 38, 267-324.
70. Pei, H.; Allison, S.; Haynes, B. M. H.; Augustin, D. J. Phys. Chem. B 2009, 113, 2564-2571.
71. Becker, R. S.; Demelo, J. S.; Macanita, A. L.; Elisei, F. Pure Appl. Chem. 1995, 67, 9-16.
72. Turro, N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991.
73. Yassar, A.; Horowitz, G.; Valat, P.; Wintgens, V.; Hmyene, M.; Deloffre, F.; Srivastava, P.; Lang, P.; Garnier, F. J. Phys. Chem. 1995, 99, 9155-9159.
74. Mcrae, E. G.; Kasha, M. J. Chem. Phys. 1958, 28, 721-722.
75. Harada, N.; Nakanishi, K. Circular Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry; University Science Books: Mill Valley, CA, 1983.
76. Circular dichroism of gel samples can sometimes contain linear dichroism (LD) effects from anisotropic alignment of nanostructures with respect to the polarized light. Although we cannot completely rule out the possibility of LD interference in Figure 5d, we examined the toluene gel of 1 under polarized microscopy and did not observe any birefringence. This is a strong indication of the absense of macroscopic anisotropic domains of nanofibers within the gel. Therefore, we conclude that the CD spectra obtained should not exhibit significant LD effects. For more references, see ref 75 and Circular Dichroism & Linear Dichroism; Oxford University Press: New York, 1997.
77. Khairutdinov, R. F.; Serpone, N. J. Phys. Chem. B 1997, 101, 2602-2610.
78. Wang, M. M.; Silva, G. L.; Armitage, B. A. J. Am. Chem. Soc. 2000, 122, 9977-9986.
79. Demir, M. M.; Ozen, B.; Ozcelik, S. J. Phys. Chem. B 2009, 113, 11568-11573.
80. Maiti, N. C.; Mazumdar, S.; Periasamy, N. J. Phys. Chem. B 1998, 102, 1528-1538.
81. De Luca, G.; Romeo, A.; Villari, V.; Micali, N.; Foltran, I.; Foresti, E.; Lesci, I. G.; Roveri, N.; Zuccheri, T.; Scolaro, L. M. J. Am. Chem. Soc. 2009, 131, 6920-6921.
82. Wurthner, F.; Bauer, C.; Stepanenko, V.; Yagai, S. AdV. Mater. 2008, 20, 1695-1698.
83. Da Como, E.; Loi, M. A.; Murgia, M.; Zamboni, R.; Muccini, M. J. Am. Chem. Soc. 2006, 128, 4277-4281.
84. Yao, H.; Domoto, K.; Isohashi, T.; Kimura, K. Langmuir 2005, 21, 1067-1073.
85. Chowdhury, A.; Wachsmann-Hogiu, S.; Bangal, P. R.; Raheem, I.; Peteanu, L. A. J. Phys. Chem. B 2001, 105, 12196-12201.
86. Zhang, L.; Liu, M. H. J. Phys. Chem. B 2009, 113, 14015-14020.
87. Cardoso, M. B.; Smolensky, D.; Heller, W. T.; O'Neill, H. J. Phys. Chem. B 2009, 113, 16377-16383.
88. Delannoy, G. H. P. In Handbook of Oligo- and Polythiophenes; Fichou, D., Ed.; Wiley-VCH: Weinheim, New York, Chichester, Brisbane, Singapore, Toronto, 1999, p 283-316.
89. Cornil, J.; Bredas, J. L. Adv. Mater. 1995, 7, 295-297.
90. Ehrendorfer, C.; Karpfen, A. J. Phys. Chem. 1994, 98, 7492-7496.
91. Facchetti, A.; Yoon, M. H.; Stern, C. L.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480-13501.