Study of hopping transport in long oligothiophenes and oligoselenophenes: Dependence of reorganization energy on chain length

Chemistry - A European Journal

Volumn 14, Issue 22, 2008, Pages 6734-6741

  Zade, Sanjio S ^a,b   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

Author keywords

Charge transfer; Density functional calculations; Oligoselenophenes; Oligothiophenes; Semiconductors

Indexed keywords

OLIGOMERS; POLYMERS; POSITIVE IONS; SULFUR COMPOUNDS;

CHARGE TRANSFER; DENSITY FUNCTIONAL CALCULATIONS; OLIGOSELENOPHENES; OLIGOTHIOPHENES; SEMICONDUCTORS;

BOND LENGTH;

EID: 53849132691     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200701182     Document Type: Article

References (96)

1. a) Electronic Materials: The Oligomer Approach (Eds.: K. Müllen, G. Wegner), Wiley-VCH. Weinheim, 1998;
2. b) Handbook of Oligo-and Polythiophenes (Ed.: D. Fichou), Wiley-VCH, Weinheim, 1999;
3. c) Handbook of Conducting Polymers. 2nd ed. (Eds.: T. A. Skotheim, R. L. Elsenbaumer, J. R. Reynolds), Marcel Dekker, New York, 1998.
4. a) I. F. Perepichka, D. F. Perepichka, H. Meng, F. Wudl, Adv. Mater. 2005, 17, 2281-2305;
5. b) P. K. H. Ho, J.-S. Kim, J. H. Burroughes, H. Becker, S. F. Y. Li, T. M. Brown, F. Cacialli, R. H. Friend, Nature 2000, 404, 481-484;
6. c) G. Barbarella, M. Melucci, G. Sotgiu, Adv. Mater. 2005, 17, 1581-1593.
7. Y. Shirota, H. Kageyama, Chem. Rev. 2007, 107, 953-1010.
8. a) H. E. Katz, J. Mater. Chem. 1997, 7, 369-376;
9. b) G. Horowitz, Adv. Mater. 1998, 10, 365-377;
10. c) H. E. Katz, A. Dodabalapur, Z. Bao, in Handbook of Oligo- and Polythiophenes (Ed.: D. Fichou), Wiley-VCH, Weinheim, 1999, 459-489;
11. d) H. E. Katz, Z. Bao, J. Phys. Chem. B 2000, 104, 671-678;
12. e) H. E. Kalz, Z. Bao, S. L. Gilat. Acc. Chem. Res. 2001, 34, 359-369;
13. f) C. D. Dimitrakopoulos, P. R. L. Malenfant, Adv. Mater. 2002, 14, 99-117;
14. g) C. R. Newman, C. D. Frisbie, D. A. da Silva Filho, J. L. Brédas, P. C. Ewbank, K. R. Mann, Chem. Mater. 2004, 16, 4436-4451;
15. h)H. E. Katz, Chem. Mater. 2004, 16, 4748-4756.
16. A. R. Murphy, J. M. J. Frechet, Chem. Rev. 2007, 107, 1066-1096.
17. a) C. J. Brabec, N. S. Sariciftci, J. C. Hummelen, Adv. Funct. Mater. 2001, 11, 15-26;
18. b) H. Hoppe, N. S. Sariciftci, J. Mater. Res. 2004, 19, 1924-1945.
19. F. Wurthner, Angew. Chem. 2001, 113, 1069-1071;
20. Angew. Chem. Int. Ed. 2001, 40, 1037-1039.
21. M. Bendikov, F. Wudl, D. F. Perepichka, Chem. Rev. 2004, 104, 4891 -4946.
22. a) T. W. Kelley, D. V. Muyres, P. F. Baude, T. P. Smith, T. D. Jones, MRS Symposium Proceedings 2003, 771, 169-179;
23. b) T.W. Kelley, L. D. Boardman, T. D. Dunbar, D. V. Muyres, M. J. Pellerite, T. P. Smith, J. Phys. Chem. B 2003, 107, 5877-5881.
24. O. D. Jurchescu, J. Bass, T. T. M. Palstra, Appl. Phys. Lett. 2004, 84, 3061-3063.
25. a) J. E. Anthony, J. S. Brooks, D. L. Eaton, S. R. Parkin, J. Am. Chem. Soc 2001, 123, 9482-9483;
26. b) C. D. Sheraw, T.N. Jackson, D. L. Eaton, J. E. Anthony, Adv. Mater. 2003, 15, 2009-2011;
27. c) C. R. Swartz, S. R. Parkin, J. E. Bullock, J. E. Anthony, A. C. Mayer, G. G. Malliaras, Org. Lett. 2005, 7, 3163-3166;
28. d) M. M. Payne, S. R. Parkin, J. E. Anthony, C. C. Kuo, T. N. Jackson, J. Am. Chem. Soc 2005, 127, 4986-4987.
29. a) H. Meng, M. Bendikov, G. Mitchell, R. Helgeson, F. Wudl, Z. Bao, T. Siegrist, C. Kloc, C.-H. Chen, Adv. Mater. 2003, 15, 1090-1093;
30. b) H. Moon, R. Zeis, E.-J. Borkent, C. Besnard, A. J. Lovinger, T. Siegrist, C. Kloc, Z. Bao, J. Am. Chem. Soc. 2004, 126, 15322-15323;
31. c) J. Jiang, B. R. Kaafarani, D.C. Neckers, J. Org. Chem. 2006, 71, 2155-2158.
32. a) V. Podzorov, S. Sysoev, E. Loginova, V. Pudalov, M. Gershenson, Appl. Phys. Lett. 2003, 83, 3504-3506;
33. b) V. Podzorov, V. Pudalov, M. Gershenson, Appl. Phys. Lett. 2003, 82, 1739-1741.
34. V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson, J. A. Rogers, Science 2004, 303, 1644-1646.
35. a) F. Gamier, Chem. Phys. 1998, 227, 253-262;
36. b) G. Horowitz, X. Peng, D. Fichou, F. Gamier, J. Appl. Phys. 1990, 67, 528-532;
37. c) G. Horowitz, R. Hajlaoui, R. B. Bouchriha, M. Hajlaoui, Adv. Mater. 1998, 10, 923-927;
38. d) M. Melucci, M. Gazzano, G. Barbarella, M. Cavallini, F. Biscarini, P. Maccagnani, P. Ostoja, J. Am. Chem. Soc. 2003, 125, 10266-10274;
39. e) A. R. Murphy, J. M. J. Fréchet, P. Chang, J. Lee, V. Subramanian, J. Am. Chem. Soc. 2004, 126, 1596-1597.
40. Z. Bao, A. Dodabalapur, A. J. Lovinger, Appl. Phys. Lett. 1996, 69, 4108-4110.
41. a) I. McCulloch, C. Bailey, M. Giles, M. Heeney, I. Love. M. Shkunov, D. Sparrowe, S. Tierney, Chem. Mater. 2005, 17, 1381-1385;
42. b) Y. Wu, P. Liu, S. Gardner, B. S. Ong, Chem. Mater. 2005, 17, 221-223;
43. c) H. Sirringhaus, Adv. Mater. 2005, 17, 2411 -2425.
44. B. S. Ong, Y. L. Wu, P. Liu, S. Gardner, J. Am. Chem. Soc. 2004, 126, 3378-3379.
45. I. McCulloch, M. Heeney, C. Bailey, K. Genevicius, I. MacDonald, M. Shkunov, D. Sparrowe, S. Tierney, R. Wagner, W. Zhang, M. L. Chabinyc, R. J. Kline, M. D. McGehee, M. F. Toney. Nat. Mater. 2006, 5, 328-333.
46. See for example, H. Meng, Z. Bao, A. J. Lovinger, B.-C. Wang, A. M. Mujsce, J. Am. Chem. Soc. 2001, 123, 9214-9215.
47. Y. Kunugi, K. Takimiya, K. Yamane, K. Yamashita, A. Aso, T. Ostubo, Chem. Mater. 2003, 15, 6-7.
48. K. Takimiya, Y. Kunugi, Y. Konda, N. Niihara, T. Otsubo, J. Am. Chem. Soc. 2004, 126, 5084-5085.
49. a) D. J. Crouch, P. J. Skabara, J. E. Lohr, J. J. W. McDouall, M. Heeney, I. McCulloch, D. Sparrowe, M. Shkunov, S. J. Coles, P. N. Horton, M. B. Hursthouse, Chem. Mater. 2005, 17, 6567-6578;
50. b) K. Takimiya, Y. Kunugi, Y. Konda, H. Ebata, Y. Toyoshima, T. Otsubo, J. Am. Chem. Soc. 2006, 128, 3044-3050;
51. c) Y. M. Kim, E. Lim, I.-N. Kang, B.-J. Jung, J. Lee, B. W. Koo, L.-M. Do, H.-K. Shim, Macro-molecules 2006, 39, 4081-4085;
52. d) K. Takimiya, Y. Konda, H. Ebata, T. Otsubo, Y. Kunugi, Mol. Cryst. Liq. Cryst. 2006, 455, 361-365.
53. For the most recent review on charge transport in organic semiconductors, see: V. Coropceanu, J. Cornil, D. A. da Silva Filho, Y. Olivier, R. Silbey, J. L. Bredas, Chem. Rev. 2007, 107, 926-952, and references therein.
54. J. L. Brédas, D. Beljonne, V. Coropceanu, J. Cornil. Chem. Rev. 2004, 104, 4971-5003.
55. a) G. R. Hutchison, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 2005, 127, 2339-2350;
56. b) G. R. Hutchison, M. A. Ratner, T. J. Marks, J. Am. Chem. Soc. 2005, 127, 16866-16881;
57. c) J. L. Brédas, J. P. Calbert, D. A. da Silva Filho, J. Cornil, Proc. Natl. Acad. Sci. USA 2002, 99, 5804-5809.
58. E.-G. Kim, V. Coropceanu, N. E. Gruhn, R. S. Sánchez-Carrera, R. Snoeberger, A. J. Matzger, J-L. Brédas, J. Am. Chem. Soc. 2007, 129, 13072-13081.
59. a) R. A. Marcus, H. Eyring, Annu. Rev. Phys. Chem. 1964, 15, 155-196;
60. b) H. M. McConnell, J. Chem. Phys. 1961, 35, 508-515;
61. c) N. S. Hush, J. Chem. Phys. 1958, 28, 962-972;
62. d) R. A. Marcus, J. Chem. Phys. 1956, 24, 966-978.
63. S. S. Zade, M. Bendikov, Org. Lett. 2006, 8, 5243-5246.
64. a) G. R. Hutchison, Y.-J. Zhao, B. Delley, A.J. Freeman, M. A. Ratner, T.J. Marks, Phys. Rev. B 2003, 68, 035204-1-035204-13;
65. b) U. Salzner, O. Karalti, S. Durdagi, J. Mol. Model. 2006, 12, 687-701;
66. c) J. Gierschner, J. Cornil, H.-J. Egelhaaf, Adv. Mater. 2007, 19, 173-191.
67. a) U. Salzner, P. G. Pickup, R. A. Poirier, J.B. Lagowski, J. Phys. Chem. A 1998, 102, 2572-2578;
68. b) S. Yang, P. Olishevski, M. Kertesz, Synth. Met. 2004, 141, 171-177;
69. c) M. Kertesz, C. H. Choi, S. Yang, Chem. Rev. 2005, 105, 3448-3481.
70. Gaussian03, RevisionC.02, M.J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A.D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford, CT, 2004.
71. a) R. G. Parr, W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York. 1989;
72. b) W. Koch, M. C. Holthausen, A Chemist's Guide to Density Functional Theory, Wiley-VCH, Weinheim, 2000.
73. a) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789;
74. b) A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652.
75. N. E. Gruhn, D. A. da Silva Filho, T. G. Bill, M. Malagoli, V. Coropceanu, A. Kahn, J. L. Brédas, J. Am. Chem. Soc 2002, 124, 7918-7919.
76. 2h constrained geometries.
77. For a detailed study on the twisting energies of oligothiophenes and their cation radicals, see: S.S. Zade, M. Bendikov, Chem. Eur. J. 2007, 13, 3688-3700.
78. V. M. Geskin, J. Cornil, J. L. Brédas, Chem. Phys. Lett. 2005, 403, 228-231.
79. M. Malagoli, J. L. Brédas, Chem. Phys. Lett. 2000, 327, 13-17.
80. [26a]
81. We note, however, that achievement of an "ideally ordered" polymer is currently not a practical possibility, although synthetic methods for synthesis of conjugated polymers with a high degree of order were reported. H. Meng, D. F. Perepichka, M. Bendikov, F. Wudl, G. Z. Pan, W. Yu, W. Dong, S. Brown, J. Am. Chem. Soc. 2003, 125, 15151-15162.
82. In experimentally studied doped conducting polymers the polaron length should be shorter than in calculations on gas-phase oligomers, which are performed without the presence of counterion or dopant, For effect of dopant see: N. Zamoshchik, U. Salzner, M. Bendikov, J. Phys. Chem. C. 2007, 112, 8408-8418. However, in the case of active semiconductors in OFETs the polaron length should be similar to that from calculations, since counterions are not present in both calculations and OFET.
83. However, for such a system, the charge density might also be low.
84. It was recently suggested that disorder can even increase the mobility of conjugated polymers: S. Athanasopoulos, J. Kirkpatrick, D. Martínez., J. M. Frost, C. M. Foden. Alison B. Walker, J. Nelson, Nano Lett. 2007, 7, 1785-1788.
85. A. Salleo, T. W. Chen, A. R. Volkel, Y. Wu, P. Liu, B. S. Ong, R. A. Street. Phys. Rev. B 2004, 70, 115311/1-115311/10.
86. P. Prins, F. C. Grozema, F. Galbrecht, U. Scherf, L. D. A. Siebbeles, J. Phys. Chem. C 2007, 111, 11104-11112.
87. D.M. DeLongchamp, R.J. Kline, E. K. Lin, D. A. Fischer, L. J. Richter, L. A. Lucas, M. Heeney, I. McCulloch, J. E. Northrup, Adv. Mater. 2007, 19, 833-837.
88. S. S. Zade, M. Bendikov, J. Org. Chem. 2006, 71, 2972-2981.
89. [48] so that oligomers larger than 20-mers might exhibit a linear correlation for reorganization energy versus 1/n.
90. N→x δL/δN = 0.
91. Similar results were reported for short oligothiophenes: G. Moro, G. Scalmani, U. Cosentino, D. Pitea, Synth. Met. 2000, 108, 165-172.
92. S. S. Zade, M. Bendikov, unpublished results. For similar studies on oligo(phenylene vinylene) cation radicals, see V. M. Geskin, F. C. Grozema, L. D. A. Siebbeles, D. Beljonne, J. L. Brédas, J. Cornil, J. Phys. Chem. B 2005, 109, 20237-20243.
93. See also ref. [26a]
94. The most detailed theoretical study addressing the dependence of theoretical levels on delocalization in conjugated systems is that of T. Bally, D. A. Hrovat, W. T. Borden, Phys Chem. Chem. Phys. 2000, 2, 3363-3371, who studied the spin distribution in polyenyl radicals. Unfortunately, DFT and HF-based methods are the only practical options to study long oligothiophenes and oligoseleno-phenes.
95. Note that the second, rough, assumption is solely to simplify the mathematical equations. Our conclusions are also valid for the more realistic situation in which charge is not equally distributed inside the rings, but is equally distributed between all rings.
96. U. Salzner, P. G. Pickup, R. A. Poirier, J. B. Lagowski, J. Phys. Chem. A 1998, 102, 2572-2578, and references therein.