Accurate prediction of band gaps in neutral heterocyclic conjugated polymers

Journal of Physical Chemistry A

Volumn 106, Issue 44, 2002, Pages 10596-10605

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

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BAND GAPS;

COMPUTATIONAL METHODS; DATA STRUCTURES; ENERGY GAP; ERROR ANALYSIS; OPTICAL PROPERTIES; POLYPYRROLES;

OLIGOMERS;

EID: 0037038507     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp025999m     Document Type: Article

References (70)

1. Shirakawa, H.; Louis, E.J.; MacDiarmid, A.G.; Chiang, C.K.; Heeger, A.J. J. Chem. Soc. Chem. Commun. 1977, 578-580.
2. Heeger, A.J. Angew. Chem., Int. Ed. Engl. 2001, 40, 2591-2611.
3. MacDiarmid, A.G. Angew. Chem., Int. Ed. Engl. 2001, 40, 2581-2590.
4. Shirakawa, H. Angew. Chem., Int. Ed. Engl. 2001, 40, 2575-2580.
5. Bäuerle, P. Sulfur-Containing Oligomers. In Electronic Materials: The Oligomer Approach; Müllen, K., Egner, G., Eds.; Wiley-VCH: Weinheim, 1998; pp 105-197.
6. McCullough, R.D. Adv. Mater. 1998, 10, 93.
7. Groenendaal, L.; Meijer, E.W.; Vekemans, J.A.J.M. Nitrogen-Containing Oligomers. In Electronic Materials: The Oligomer Approach; Müllen, K., Egner, G., Eds.; Wiley-VCH: Weinheim, 1998; pp 235-272.
8. Glenis, S.; Benz, M.; LeGoff, E.; Schindler, J.L.; Kannewurf, C.R.; Kanatzidis, M.G. J. Am. Chem. Soc. 1993, 115, 12519-12525.
9. Seixas de Melo, J.; Elisei, F.; Gartner, C.; Gaetano Aloisi, G.; Becker, R.S. J. Phys. Chem. A 2000, 104, 6907-6911.
10. Kauffmann, T.; Lexy, H. Chem. Ber. 1981, 114, 3667-3673.
11. Nalwa, H.S. Handbook of Advanced Electronic and Photonic Materials and Devices; Academic: San Diego, CA, 2000.
12. Müllen, K.; Wegner, G. Electronic Materials: The Oligomer Approach; Wiley-VCH: Weinheim, New York, 1998.
13. Brédas, J.L.; Cornil, J.; Beljonne, D.; dos Santos, D.; Shuai, Z.G. Acc. Chem. Res. 1999, 32, 267-276.
14. Alper, J. Science 1989, 246, 208-210.
15. Gamier, F. Chem. Phys. 1998, 227, 253-262.
16. Würthner, F. Angew. Chem., Int. Ed. Engl. 2001, 40, 1037.
17. Ho, P.K.H.; Kim, J.-S.; Burroughes, J.H.; Becker, H.; Li, S.F.Y.; Brown, T.M.; Cacialli, F.; Friend, R.H. Nature 2000, 404, 481-484.
18. Pinner, D.J.; Friend, R.H.; Tessler, N. Appl. Phys. Lett. 2000, 76, 1137-1139.
19. Inganäs, O.; Berggren, M.; Andersson, M.R.; Gustafsson, G.; Hjertberg, T.; Wennerström, O.; Dyreklev, P.; Granström, M. Synth. Met. 1995, 71, 2121-2124.
20. Granström, M.; Petrisch, K.; Arias, A.C.; Lux, A.; Andersson, M.R.; Friend, R.H. Nature 1998, 395, 257.
21. Ding, L.; Jonforsen, M.; Roman, L.S.; Andersson, M.R.; Inganäs, O. Synth. Met. 2000, 110, 113-140.
22. Noda, T.; Ogawa, H.; Noma, N.; Shirota, Y. J. Mater. Chem. 1999, 9, 2177-2181.
23. Grem, G.; Leising, G. Synth. Met. 1993, 57, 4105-4110.
24. Berggren, M.; Inganäs, O.; Gustafsson, G.; Rasmusson, J.; Andersson, M.R.; Hjertberg, T.; Wennerström, O. Nature 1994, 372, 444-446.
25. Campbell, I.H.; Smith, D.L. Electrical Transport in Organic Semiconductors. In Topics in High Field Transport in Semiconductors; Brennan, K.F., Ruden, P.P., Eds.; World Scientific: London, 2001; Vol. 22, pp 223-249.
26. Mitschke, U.; Bäuerle, P. J. Mater. Chem. 2000, 10, 1471-1507.
27. Kalinowski, J. J. Phys. D: Appl. Phys. 1999, 32, R179-R250.
28. Grem, G.; Leditzky, G.; Ullrich, B.; Leising, G. Adv. Mater. 1992, 4, 36-7.
29. Nelson, J. Science 2001, 293, 1059-1060.
30. Di Marco, P.; Giro, G. Appl. Phys. (N.Y.) 1994, 4, 791-823.
31. Roncali, J. Chem. Rev. 1997, 97, 173-205.
32. Salzner, U.; Lagowski, J.B.; Pickup, P.G.; Poirier, R.A. Synth. Met. 1998, 96, 177-189.
33. Salzner, U.; Pickup, P.G.; Pokier, R.A.; Lagowski, J.B. J. Phys. Chem. A 1998, 102, 2572-2578.
34. Telesca, R.; Bolink, H.; Yunoki, S.; Hadziioannou, G.; Van Duijnen, P.T.; Snijders, J.G.; Jonkman, H.T.; Sawatzky, G.A. Phys. Rev. B 2001, 6315, 5112.
35. Hutchison, G.R.; Zhao, Y.-J.; Freeman, A.J.;Ratner, M.A.; Marks, T.J. submitted.
36. Ridley, J.; Zerner, M. Theor. Chim. Acta 1973, 32, 111-134.
37. Hicks, R.G.; Nodwell, M.B. J. Am. Chem. Soc. 2000, 122, 6746-6753.
38. Garcia, P.; Pernaut, J.-M.; Hapiot, P.; Wintgens, V.; Valat, P.; Garnie, F.; Delabouglise, D. J. Phys. Chem. 1993, 97, 513-516.
39. Zotti, G.; Zecchin, S.; Schiavon, G.; Groenendaal, L.B. Chem. Mater. 2000, 12, 2996-3005.
40. Miller, L.L.; Yu, Y. J. Org. Chem. 1995, 60, 6813-6819.
41. Groenendaal, L.; Jonas, F.; Freitag, D.; Pielartzik, H.; Reynolds, J.R. Adv. Mater. 2000, 12, 481-494.
42. Sotzing, G.A.; Reynolds, J.R.; Steel, P.J. Chem. Mater. 1996, 8, 882-889.
43. Wang, C.; Schindler, J.L.; Kannewurf, C.R.; Kanatzidis, M.G. Chem. Mater. 1995, 7, 58-68.
44. Mohanakrishnan, A.K.; Hucke, A.; Lyon, M.A.; Lakshmikantham, M.V.; Cava, M.P. Tetrahedron 1999, 55, 11745-11754.
45. Schottland, P.; Zong, K.; Gaupp, C.L.; Thompson, B.C.; Thomas, C.A.; Giurgiu, I.; Hickman, R.; Abboud, K.; Reynolds, J.R. Macromolecules 2000, 33, 7051-7061.
46. Turbiez, M.; Frère, P.; Blanchard, P.; Roncali, J. Tetrahedron Lett. 2000, 41, 5521-5525.
47. Demanze, F.; Cornil, J.; Garnier, F.; Horowitz, G.; Valat, P.; Yassar, A.; Lazzaroni, R.; Brédas, J.-L. J. Phys. Chem. B 1997, 101, 4553-4558.
48. Fichou, D.; Teulade-Fichou, M.-P.; Horowitz, G.; Demanze, F. Adv. Mater. 1997, 9, 75-80.
49. Fichou, D.; Horowitz, G.; Xu, B.; Gamier, F. Synth. Met. 1990, 39, 243-59.
50. Dewar, M.J.S.; Zoebisch, E.G.; Healy, E.F.; Stewart, J.J.P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
51. Schmidt, M.W.; Baldridge, K.K.; Boatz, J.A.; Elbert, S.T.; Gordon; M.S.; Jensen, J.H.; Koseki, S.; Matsunaga, N.; Nguyen, K.A.; Su, S.J.; Windus, T.L.; Dupuis, M.; Montgomery, J.A. J. Comput. Chem. 1993, 14, 1347-1363.
52. Becke, A.D. J. Chem. Phys 1993, 98, 5648-5652.
53. Lee, C.; Yang, W.; Parr, R.G. Phys. Rev. B 1988, 37, 785-789.
54. Kong, J.; White, C.A.; Krylov, A.I.; Sherrill, C.D.; Adamson, R.D.; Furlani, T.R.; Lee, M.S.; Lee, A.M.; Gwaltney, S.R.; Adams, T.R.; Ochsenfeld, C.; Gilbert, A.T.B.; Kedziora, G.S.; Rassolov, V.A.; Maurice, D.R.; Nair, N.; Shao, Y.; Besley, N.A.; Maslen, P.E.; Dombroski, J.P.; Dachsel, H.; Zhang, W.M.; Korambath, P.P.; Baker, J.; Byrd, E.F.C.; Van Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C.P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B.G.; Gill, P.M.W.; Head-Gordon, M.; Pople, J.A. J. Comput. Chem. 2000, 21, 1532-1548.
55. Tretiak, S.; Saxena, A.; Martin, R.L.; Bishop, A.R. Chem. Phys. Lett. 2000, 331, 561-568.
56. Mukamel, S.; Tretiak, S.; Wagersteiter, T.; Chernyak, V. Science 1997, 277, 781-787.
57. Chernyak, V.; Schulz, M.F.; Mukamel, S.; Trtiak, S.; Tsiper, E.V. J. Chem. Phys. 2000, 113, 36-43.
58. Hirata, S.; Head-Gordon, M. Chem. Phys. Lett. 1999, 314, 291-299.
59. Hsu, C.-P.; Hirata, S.; Head-Gordon, M. J. Phys. Chem. A 2001, 105, 451-458.
60. Hirata, S.; Lee, T.J.; Head-Gordon, M. J. Chem. Phys. 1999, 111, 8904-8912.
61. Stratmann, R.E.; Scuseria, G.E.; Frisch, M.J. J. Chem. Phys. 1998, 109, 8218-8224.
62. Baker, J.D.; Zerner, M.C. J. Phys. Chem. 1991, 95, 8614-8619.
63. Linderberg, J.; Öhrn, Y. Propagators in Quantum Chemistry; Academic Press: London, New York, 1973.
64. Quattrocchi, C.; Lazzaroni, R.; Bredas, J.L. Chem. Phys. Lett. 1993, 208, 120-4.
65. Nino, A.; Munoz-Caro, C.; Senent, M.L. THEOCHEM 2000, 530, 291-300.
66. Mohamed, A.A. Int. J. Quantum Chem. 2000, 79, 367-377.
67. Carballeira, L.; Perez-Juste, I. J. Comput. Chem. 1998, 19, 961-976.
68. Handbook of Chemistry and Physics; CRC Press: Boca Raton, FL, 1995.
69. Yaliraki, S.N.; Silbey, R.J. J. Chem. Phys. 1996, 104, 1245-1253.
70. Merrill, B.A.; LeGoff, E. J. Org. Chem. 1990, 55, 2904-2908.