Intermolecular charge transfer between heterocyclic oligomers. Effects of heteroatom and molecular packing on hopping transport in organic semiconductors

Journal of the American Chemical Society

Volumn 127, Issue 48, 2005, Pages 16866-16881

  Hutchison, Geoffrey R ^a,b   Ratner, Mark A ^a   Marks, Tobin J ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

^b Baker Laboratory ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; ELECTROSTATICS; HOLE MOBILITY; MOLECULAR DYNAMICS; MULTIVARIABLE CONTROL SYSTEMS;

ELECTROSTATIC REPULSION; HOLE TRANSFER; INTERMOLECULAR CHARGE TRANSFER; INTERMOLECULAR ORIENTATION;

OLIGOMERS;

HETEROCYCLIC COMPOUND; OLIGOMER; POLYMER;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; ENERGY; MULTIVARIATE ANALYSIS; REACTION ANALYSIS; SEMICONDUCTOR; STRUCTURE ANALYSIS;

EID: 28844434139     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0533996     Document Type: Article

References (161)

1. (a) Ho, P. K. H.; Kim, J.-S.; Burroughes, J. H.; Beeker, H.; Li, S. F. Y.; Brown, T. M.; Cacialli, F.; Friend, R. H. Nature 2000, 404, 481.
2. (b) Pinner, D. J.; Friend, R. H.; Tessler, N. Appl. Phys. Lett. 2000, 76, 1137.
3. (c) Inganäs, O.; Berggren, M.; Andersson, M. R.; Gustafsson, G.; Hjertberg, T.; Wennerström, O.; Dyreklev, P.; Granström, M. Synth. Met. 1995, 71, 2121.
4. (a) Ding, L.; Jonforsen, M.; Roman, L. S.; Andersson, M. R.; Inganas, O. Synth. Met. 2000, 110, 113.
5. (b) Granström, M.; Petrisch, K.; Arias, A. C.; Lux, A.; Andersson, M. R.; Friend, R. H. Nature 1998, 395, 257.
6. (a) Würthner, F. Angew. Chem., Int. Ed. 2001, 40, 1037.
7. (b) Garnier, F. Chem. Phys. 1998, 227, 253.
8. (c) Katz, H. E. J. Mater. Chem. 1997, 7, 369.
9. (a) Prigodin, V. N.; Epstein, A. J. Synth. Met. 2001, 125, 43.
10. (b) Joo, J.; Lee, J. K.; Baeck, J. S.; Kim, K. H.; Oh, E. J.; Epstein, J. Synth. Met. 2001, 117, 45.
11. (c) Hilt, O.; Reedijk, J. A.; Martens, H. C. F.; Brom, H. B.; Michels, M. A. J. Phys. Status Solidi B 2000, 218, 279.
12. (d) Reedijk, J. A.; Martens, H. C. F.; Brom, H. B.; Michels, M. A. J. Phys. Rev. Lett. 1999, 83, 3904.
13. (e) Kohlman, R. S.; Epstein, A. J. In Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; pp 85.
14. (f) Menon, R.; Yoon, C. O.; Moses, D.; Heeger, A. J. In Handbook of Conducting Polymers, 2nd ed.: Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998; p 27.
15. (g) Epstein, A. J. Mater. Res. Bull. 1997, 22, 16.
16. (a) Epstein, A. J.; Lee, W. P.; Prigodin, V. N. Synth. Met. 2001, 117, 9.
17. (b) Reedijk, J. A.; Martens, H. C. F.; van Bohemen, S. M. C.; Hilt, O.; Brom, H. B.; Michels, M. A. J. Synth. Met. 1999, 101, 475.
18. (c) Mott, N. F.; Davis, E. A. Electronic Processes in Non-Crystalline Materials, 2d ed.; Oxford University Press: Oxford, 1979.
19. (a) Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals and Polymers, 2nd ed.; Oxford University Press: New York, 1999.
20. (b) Pope, M.; Swenberg, C. E. Electronic Processes in Organic Crystals; Oxford University Press: New York, 1982.
21. Cheng, Y. C.; Silbey, R. J.; da Silva, D. A.; Calbert, J. P.; Cornil, J.; Brédas, J. L. J. Chem. Phys. 2003, 118, 3764.
22. Brédas, J. L.; Calbert, J. P.; da Silva, D. A.; Cornil, J. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5804.
23. Brédas, J. L.; Beljonne, D.; Cornil, J.; Calbert, J. P.; Shuai, Z.; Silbey, R. Synth. Met. 2001, 125, 107.
24. Cornil, J.; Beljonne, D.; Calbert, J. P.; Brédas, J. L. Adv. Mater. 2001, 13, 1053.
25. Berlin, Y. A.; Hutehison, G. R.; Rempala, P.; Ratner, M. A.; Michl, J. J. Phys. Chem. A 2003, 107, 3970.
26. (a) Bixon, M.; Jortner, J. Adv. Chem. Phys. 1999, 106, 35.
27. (b) Newton, M. D. Adv. Chem. Phys. 1999, 106, 303.
28. (c) Barbara, P. F.; Meyer, T. J.; Ratner, M. A. J. Phys. Chem. 1996, 100, 13148.
29. (d) Marcus, R. A.; Eyring, H. Annu. Rev. Phys. Chem. 1964, 15, 155.
30. (e) McConnell, H. M. J. Chem. Phys. 1961, 35, 508.
31. (f) Hush, N. S. J. Chem. Phys. 1958, 28, 962.
32. (g) Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
33. (h) Marcus, R. A. Rev. Mod. Phys. 1993, 65, 599.
34. (i) Newton, M. D.; Sutin. N. Annu. Rev. Phys. Chem. 1984, 35, 437.
35. Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 2339.
36. Deng, W. Q.; Goddard, W. A. J. Phys. Chem. B 2004, 108, 8614.
37. (a) Silerova, R.; Kalvoda, L.; Neher, D.; Ferencz, A.; Wu, J.; Wegner, G. Chem. Mater. 1998, 10, 2284.
38. (b) Adams, P. N.; Laughlin, P. J.; Monkman, A. P.; Bernhoeft, N. Solid State Commun. 1994, 91, 875.
39. (c) Ostrick, J. R.; Dodabalapur, A.; Torsi, L.; Lovinger, A. J.; Kwock, E. W.; Miller, T. M.; Calvin, M.; Berggren, M.; Katz, H. E. J. Appl. Phys. 1997, 81, 6804.
40. (a) Facchetti, A.; Deng, Y.; Wang, A.; Koide, Y.; Sirringhaus, H.; Marks, T. J.; Friend, R. H. Angew. Chem., Int. Ed. 2000, 39, 4547.
41. (b) Facchetti, A.; Mushrush, M.; Katz, H. E.; Marks, T. J. Adv. Mater. 2003, 15, 33.
42. (c) Jones, B. A.; Ahrens, M. J.; Yoon, M.-H.; Facchetti, A.; Marks, T. J.; Wasielewski, M. R. Angew. Chem. Int. Ed. 2004, 43, 6363-6366.
43. (d) Yoon, M.-H.; DiBenedetto, S.; Facchetti, A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 1348-1349.
44. (e) Letizia, J. A.; Facchetti, A.; Stern, C. L.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2005, 127, 13476-14477.
45. (a) Facchetti, A.; Wang, A.; Marks, T. J. Polym. Mater. Sci. Eng. 2000, 83, 290.
46. (b) Garnier, F.; Yassar, A.; Hajlaoui, R.; Horowitz, G.; Deloffre, F.; Servet, B.; Ries, S.; Alnot, P. J. Am. Chem. Soc. 1993, 115, 8716.
47. (c) Visser, G. J.; Heeres, G. J.; Wolters, J.; Vos. A. Acta Crystallogr., Sect. B 1968, 24, 467.
48. (d) Pyrka, G. J.; Fernando, Q.; Inoue, M. B.; Inoue, M.; Velazquez, E. F. Acta Crystallogr., Sect. C 1988, 44, 562.
49. (e) Hotta, S.; Waragai, K. J. Mater. Chem. 1991, 1, 835.
50. (f) Chaloner, P. A.; Gunatunga, S. R.; Hitchcock, P. B. Acta Crystallogr., Sect. C 1994, 50, 1941.
51. (g) Pelletier, M.; Brisse, F. Acta Crystallogr., Sect. C 1994, 50, 1942.
52. (h) Horowitz, G.; Bachet, B.; Yassar, A.; Lang, P.; Demanze, F.; Fave, J.-L.; Garnier, F. Chem. Mater. 1995, 7, 1337.
53. (i) Siegrist, T.; Fleming, R. M.; Haddon, R. C.; Laudise, R. A.; Lovinger, A. J.; Katz, H. E.; Bridenbaugh, P.; Davis, D. D. J. Mater. Res. 1995, 10, 2170.
54. (j) Barbarella, G.; Zambianchi, M.; Antolini, L.; Folli, U.; Goldoni, F.; Iarossi, D.; Schenetti, L.; Bongini, A. J. Chem. Soc., Perkin Trans. 2 1995, 1869.
55. (k) Fichou, D.; Bachet, B.; Demanze, F.; Billy, I.; Horowitz, G.; Garnier, F. Adv. Mater. 1996, 8, 500.
56. (l) Siegrist, T.; Kloc, C.; Laudise, R. A.; Katz, H. E.; Haddon, R. C. Adv. Mater. 1998, 10, 379.
57. Antolini, L.; Horowitz, G.; Kouki, F.; Garnier, F. Adv. Mater. 1998, 10, 382.
58. (a) DiCesare, N.; Belletete, M.; Murrano, C.; Leclerc, M.; Durocher, G. J. Phys. Chem. A 1999, 103, 795.
59. (b) DiCesare, N.; Belletete, M.; Garcia, E. R.; Leclerc, M.; Durocher, G. J. Phys. Chem. A 1999, 103, 3864.
60. (c) DiCesare, N.; Belletete, M.; Leclerc, M.; Durocher, G. J. Phys. Chem. A 1999, 103, 803.
61. (d) Tedesco, E.; Della Salla, F.; Favaretto, L.; Barbarella, G.; Albesa-Jove, D.; Pisignano, D.; Gigli, G.; Cingolani, R.; Harris, K. D. M. J. Am. Chem. Soc. 2003, 125, 12277.
62. (a) Lin B. C.; Cheng, C. P.; Lao, Z. P. M. J. Phys. Chem. A 2003, 107, 5241.
63. (b) Malagoli, M.; Brédas, J. L. Chem. Phys. Lett. 2000, 327, 13.
64. (c) Sakanoue, K.; Motoda, M.; Sugimoto, M.; Sakaki, S. J. Phys. Chem. A 1999, 103, 5551.
65. (a) Blomgren, F.; Larsson, S. Theor. Chem. Acc. 2003, 110, 165.
66. (b) Siriwong, K.; Voityuk, A. A.; Newton, M. D.; Rosch, N. J. Phys. Chem. B 2003, 107, 2595.
67. (c) Blomgren, F.; Larsson, S.; Nelsen, S. F. J. Comput. Chem. 2001, 22, 655.
68. (d) Nelsen, S. F.; Blomgren, F. J. Org. Chem. 2001, 66, 6551.
69. (e) Klimkans, A.; Larsson, S. Int. J. Quantum Chem. 2000, 77, 211.
70. (f) Nelsen, S. F.; Trieber, D. A.; Nagy, M. A.; Konradsson. A.; Halfen, D. T.; Splan, K. A.; Pladziewicz, J. R. J. Am. Chem. Soc. 2000, 122, 5940.
71. (g) Nelsen, S. F.; Ismagilov, R. F.; Gentile, K. E.; Nagy, M. A.; Tran, H. Q.; Qu, Q.; Halfen, D. T.; Odegard, A. L.; Pladziewicz, J. R. J. Am. Chem. Soc. 1998, 120, 8230.
72. (h) Jakobsen, S.; Mikkelsen, K. V.; Pedersen, S. U. J. Phys. Chem. 1996, 100, 7411.
73. (i) Klimkans, A.; Larsson, S. Chem. Phys. 1994, 189, 25.
74. (j) Todd, M. D.; Mikkelsen, K. V. Inorg. Chim. Acta 1994, 226, 237.
75. (a) Seixas de Melo, J.; Elisei, F.; Gartner, C.; Gaetano Aloisi, G.; Becker, R. S. J. Phys. Chem. A 2000, 104, 6907.
76. (b) Fichou, D. Handbook of Oligo- and Polythiophenes; Wiley-VCH: Weinheim, New York, 1999.
77. (c) Cornil, J.; Beljonne, D.; Brédas, J. L. Electronic Materials: The Oligomer Approach; Wiley-VCH: Weinheim, Germany, 1998; p 432.
78. (d) Bäuerle, P. In Electronic Materials: The Oligomer Approach; Müllen, K., Egner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 105.
79. (e) Groenendaal, L.; Meijer, E. W.; Vekemans, J. A. J. M. In Electronic Materials: The Oligomer Approach; Müllen, K., Egner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998; p 235.
80. (f) McCullough, R. D. Adv. Mater. 1998, 10, 93.
81. (g) Glenis, S.; Benz, M.; Legoff, E.; Schindler, J. L.; Kannewurf, C. R.; Kanatzidis, M. G. J. Am. Chem. Soc. 1993, 115, 12519.
82. (h) Kauffmann, T.; Lexy, H. Chem. Ber. 1981, 114, 3667.
83. (a) Gorman, C. B.; Marder, S. R. Chem. Mater. 1995, 7, 215.
84. (b) Meyers, F.; Marder, S. R.; Pierce, B. M.; Brédas, J. L. J. Am. Chem. Soc. 1994, 116, 10703.
85. (c) Bourhill, G.; Brédas, J.-L.; Cheng, L.-T.; Marder, S. R.; Meyers, F.; Perry, J. W.; Tiemann, B. G. J. Am. Chem. Soc. 1994, 116, 2619.
86. (d) Marder, S. R.; Perry, J. W.; Bourhill, G.; Gorman, C. B.; Tiemann, B. G.; Mansour, K. Science 1993, 261, 186.
87. (e) Marder, S. R.; Perry, J. W.; Tiemann, B. G.; Gorman, C. B.; Gilmour, S.; Biddle, S. L.; Bourhill, G. J. Am. Chem. Soc. 1993, 115, 2524.
88. (f) Cui, C. X.; Kertesz, M.; Jiang, Y. J. Phys. Chem. 1990, 94, 5172.
89. (g) Lee, Y. S.; Kertesz, M. J. Chem. Phys. 1988, 88, 2609.
90. (h) Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Phys. Chem. B 2005, 109, 3126.
91. Hutchison, G. R.; Zhao, Y. J.; Delley, B.; Freeman, A. J.; Ratner, M. A.; Marks, T. J. Phys. Rev. B 2003, 68, 035204.
92. Communicated in part at: (a) Excited State Processes in Electronic and Bio-Nanomaterials, Los Alamos, August 11-16, 2003.
93. (b) ACS Prospectives Symposium "Organic Thin Film Electronics", Miami, Jan. 25-28, 2004.
94. (c) The 227th National Meeting of the ACS, Anaheim CA.; Facchetti, A.; Hutchison, G.; Yoon, M.-H.; Letizia, J.; Ratner, M. A.; Marks, T. J. Polymer Preprints, 2004, 45, 185-186.
95. (d) Sixth International Symposium on Functional π-Electron Systems, Ithaca, NY, June 14-18, 2004.
96. Kong, J. et al. J. Comput. Chem. 2000, 21, 1532.
97. (a) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
98. (b) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
99. Tsuzuki, S.; Uchimaru, T.; Sugawara, K.-i.; Mikami, M. J. Chem. Phys. 2002, 117, 11216.
100. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. J. Chem. Soc., Perkin Trans. 2 2001, 651.
101. Columberg, G.; Bauder, A. J. Chem. Phys. 1997, 106, 504.
102. (a) Park, H.; Lee, S. Chem. Phys. Lett. 1999, 301, 487.
103. (b) Stefov, V.; Pejov, L.; Soptrajanov, B. J. Mol. Struct. 2003, 649, 231.
104. Facchetti, A.; Yoon, M.-H.; Hutchison, G. R.; Stern, C. L.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13480.
105. Except where indicated, calculations use the 6-31G* basis set. We recomputed potential energy curves and surfaces with the more accurate 6-31+G* basis set and counterpoise corrections, though the increased basis set has no effect on the computed orbital energy levels, as illustrated in Figure 8.
106. Delley, B. J. Chem. Phys. 2000, 113, 7756.
107. (a) Wu, Q.; Yang, W. J. Chem. Phys. 2002, 116, 515.
108. (b) Wu, X.; Vargas, M. C.; Nayak, S.; Lotrich, V.; Scoles, G. J. Chem. Phys. 2001, 115, 8748.
109. (c) Kohn, W.; Meir, Y.; Makarov, D. E. Phys. Rev. Lett. 1998, 80, 4153.
110. (d) Zhang, Y.; Pan, W.; Yang, W. J. Chem. Phys. 1997, 107, 7921.
111. (e) Lundqvist, B. I.; Andersson, Y.; Shao, H.; Chan, S.; Langreth, D. C. Int. J. Quantum Chem. 1995, 56, 247.
112. Kurita, N.; Sekino, H. Chem. Phys. Lett. 2001, 348, 139.
113. (a) Reyes, A.; Tlenkopatchev, M. A.; Fomina, L.; Guadarrama, P.; Fomine, S. J. Phys. Chem. A 2003, 107, 7027.
114. (b) Huh, S. B.; Lee, J. S. J. Chem. Phys. 2003, 118, 3035.
115. (c) Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. J. Am. Chem. Soc. 2002, 124, 10887.
116. (d) Lee, N. K.; Park, S.; Kim, S. K. J. Chem. Phys. 2002, 116, 7910.
117. (e) Lee, N. K.; Park, S.; Kim, S. K. J. Chem. Phys. 2002, 116, 7902.
118. (a) Tsuzuki, S.; Honda, K.; Azumi, R. J. Am. Chem. Soc. 2002, 124, 12200.
119. (b) Tsuzuki, S.; Honda, K.; Uchimaru, T.; Mikami, M.; Tanabe, K. J. Am. Chem. Soc. 2002, 124, 104.
120. Tsuzuki, S.; Uchimaru, T.; Matsumura, K.; Mikami, M.; Tanabe, K. Chem. Phys. Lett. 2000, 319, 547.
121. Suhai, S. Int. J. Quantum Chem. 1992, 42, 193.
122. (a) Gruhn, N. E.; da Silva, D. A.; Bill, T. G.; Malagoli, M.; Coropceanu, V.; Kahn, A.; Brédas, J. L. J. Am. Chem. Soc. 2002, 124, 7918.
123. (b) Amashukeli, X.; Winkler, J. R.; Gray, H. B.; Gruhn, N. E.; Lichtenberger, D. L. J. Phys. Chem. A 2002, 106, 7593.
124. Ihaka, R.; Gentleman, R. J. Comput. Graph. Statist. 1996, 5, 299.
125. Spartan 02: Wavefunction, Inc.: Irvine, CA, 2000.
126. Zhan, C. G.; Nichols, J. A.; Dixon, D. A. J. Phys. Chem. A 2003, 107, 4184.
127. (a) Rienstra-Kiracofe, J. C.; Tschumper, G. S.; Schaefer, H. F.; Nandi, S.; Ellison, G. B. Chem. Rev. 2002, 102, 231.
128. (b) Rienstra-Kiracofe, J. C.; Barden, C. J.; Brown, S. T.; Schaefer, H. F. J. Phys. Chem. A 2001, 105, 524.
129. (c) de Oliveira, G.; Martin, J. M. L.; de Proft, F.; Geerlings, P. Phys. Rev. A 1999, 60, 1034.
130. (d) Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1998, 109, 42.
131. (e) DeProft, F.; Geerlings, P. J. Chem. Phys. 1997, 106, 3270.
132. (a) Muscat, J.; Wander, A.; Harrison, N. M. Chem. Phys. Lett. 2001, 342, 397.
133. (b) Hutchison, G. R. Theoretical Studies of Optics and Charge Transport in Organic Conducting Oligomers and Polymers: Rational Design of Improved Transparent and Conducting Polymers. Ph.D. Dissertation. Northwestern University, Evanston, Illinois, 2004.
134. (a) Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003.
135. (b) Curtiss, L. A.; Redfern, P. C.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 2001, 114, 108.
136. (c) Bauschlicher, C. W. Chem. Phys. Lett. 1995, 246, 40.
137. In general, this is true only if basis set superposition errors (BSSE) are taken into account, for example, with counterpoise corrections. In these systems, as discussed below, the counterpoise-corrected binding energies do not show substantially different curves or extrema than the uncorrected relative energy curves.
138. (a) van der Horst, J. W.; Bobbert, P. A.; Michels, M. A. J.; Brocks, G.; Kelly, P. S. Synth. Met. 1999, 101, 333.
139. (b) van der Horst, J. W.; Bobbert, P. A.; de Jong, P. H. L.; Michels, M. A. J.; Brocks, G.; Kelly, P. J. Phys. Rev. B 2000, 61, 15817.
140. (c) Rohlfing, M.; Louie, S. G. Phys. Rev. Lett. 1999, 82, 1959.
141. (d) Rohlfing, M.; Tiago, M. L.; Louie, S. G. Synth. Met. 2001, 116, 101.
142. (e) Ferretti, A.; Ruini, A.; Molinari, E.; Caldas, M. J. Phys. Rev. Lett. 2003, 90, 086401/1.
143. (f) Bussi, G.; Ferretti, A.; Ruini, A.; Caldas, M. J.; Molinuri, E. Adv. Solid State Phys. 2003, 43, 313.
144. (g) Ruini, A.; Bussi, G.; Ferretti, A.; Caldas, M. J.; Molinari, E. Synth. Met. 2003, 139, 755.
145. (a) Tiago, M. L.; Northrup, J. E.; Louie, S. G. Phys. Rev. B 2003, 67, 115212/1.
146. (b) Ferretti, A.; Ruini, A.; Bussi, G.; Molinari, E.; Caldas, M. J. Phys. Rev. B 2004, 69, 205205/1.
147. Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1995.
148. For more information on multivariate ANOVA or multivariate linear regression techniques used here, see for example: (a) Cobb, G. W. Introduction to Design and Analysis of Experiments; Springer: New York, 1998.
149. (b) Box, G. E. P.; Hunter, W. G.; Hunter, J. S. Statistics for Experimenters: An Introduction to Design, Data Analysis, and Model Building; Wiley: New York, 1978.
150. Granstrom, E. L.; Frisbie, C. D. J. Phys. Chem. B 1999, 103, 8842.
151. Pickholz, M.; dos Santos, M. C. THEOCHEM 2005, 717, 99.
152. Scherlis, D. A.; Marzari, N. J. Phys. Chem. B 2004, 108, 17791.
153. Calbert, J.-P.; Brédas, J.-L. Personal communication.
154. (a) Heeger, A. J. In Highly Conducting One-Dimensional Solids; Devreese, J. T., Evrard, R. P., Van Doren, V. E., Eds.; Plenum: New York, 1979; pp 69.
155. (b) Kagoshima, S.; Nagasawa, H.; Sambongi, T. One-Dimensional Conductors; Springer-Verlag: Berlin, New York, 1988.
156. Endres, R. G.; Fong, C. Y.; Yang, L. H.; Witte, G.; Woell, C. Comput. Mater. Sci. 2004, 29, 362.
157. (a) Cornil, J.; Calbert, J. P.; Brédas, J. L. J. Am. Chem. Soc. 2001, 123, 1250.
158. (b) Haddon, R. C.; Chi, X.; Itkis, M. E.; Anthony, J. E.; Eaton, D. L.; Siegrist, T.; Mattheus, C. C.; Palstra, T. T. M. J. Phys. Chem. B 2002, 106, 8288.
159. (a) Chesterfield, R. J.; Newman, C. R.; Pappenfus, T. M.; Ewbank, P. C.; Haukaas, M. H.; Mann, K. R.; Miller, L. L.; Frishie, C. D. Adv. Mater. 2003, 15, 1278.
160. (b) Pappenfus, T. M.; Chesterfield, R. J.; Frisbie, C. D.; Mann, K. R.; Casado, J.; Raff, J. D.; Miller, L. L. J. Am. Chem. Soc. 2002, 124, 4184.
161. (c) Facchetti, A.; Mushrush, M.; Yoon, M.-H.; Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc. 2004, 126, 13859.