Quantum chemical approach toward the electronic, photophysical and charge transfer properties of the materials used in organic field-effect transistors

Materials Chemistry and Physics

Volumn 138, Issue 2-3, 2013, Pages 468-478

  Chaudhry, Aijaz Rasool ^a,b   Ahmed, R ^a   Irfan, Ahmad ^b   Shaari, A ^a   Al Sehemi, Abdullah G ^b  

^a UNIVERSITI TEKNOLOGI MALAYSIA   (Malaysia)

^b KING KHALID UNIVERSITY   (Saudi Arabia)

Author keywords

Ab initio calculations; Computational techniques; Electronic materials; Luminescence; Semiconductors

Indexed keywords

AB INITIO CALCULATIONS; ADIABATIC ELECTRON AFFINITY; ADIABATIC IONIZATION POTENTIAL; CHARGE TRANSFER PROPERTIES; COMONOMERS; COMPUTATIONAL TECHNIQUE; CYCLOPENTADIENES; DENSITY FUNCTIONAL THEORIES (DFT); DISTRIBUTION PATTERNS; ELECTRON TRANSPORT MATERIALS; ELECTRONIC MATERIALS; HETEROATOMS; HIGHEST OCCUPIED MOLECULAR ORBITAL; HOLE TRANSPORTS; LOWEST UNOCCUPIED MOLECULAR ORBITAL; PHOTOPHYSICAL; PHOTOPHYSICAL PROPERTIES; PYRAZINES; PYRIDAZINE; QUANTUM CHEMICAL APPROACH; REORGANIZATION ENERGIES; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; VERTICAL ELECTRON AFFINITIES; VERTICAL IONIZATION POTENTIALS;

BENZENE; CHARGE TRANSFER; DENSITY FUNCTIONAL THEORY; IONIZATION POTENTIAL; LUMINESCENCE; MOLECULAR ORBITALS; MOLECULES; OLEFINS; ORGANIC FIELD EFFECT TRANSISTORS; ORGANIC POLLUTANTS; PYRIDINE; SEMICONDUCTOR MATERIALS; THIOPHENE;

MATERIALS PROPERTIES;

EID: 84874531056     PISSN: 02540584     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.matchemphys.2012.11.075     Document Type: Article

References (97)

1. A. Tsumura, H. Koezuka, and T. Ando Appl. Phys. Lett. 49 1986 1210 1212
2. H.E. Katz J. Mater. Chem. 7 1997 369 376
3. G. Horowitz, and M.E. Hajlaoui Adv. Mater. 12 2000 1046 1050
4. C.R. Newman, C.D. Frisbie, D.A. daSilva, J.L. Brédas, P.C. Ewbank, and K.R. Mann Chem. Mater. 16 2004 4436 4451
5. C.W. Tang, and S.A. VanSlyke Appl. Phys. Lett. 51 1987 913 915
6. P.K.H. Ho, J.S. Kim, J.H. Burroughes, H. Becker, S.F.Y. Li, T.M. Brown, F. Cacialli, and R.H. Friend Nature 404 2000 481 484
7. F. Padinger, R.S. Rittberger, and N.S. Sariciftci Adv. Funct. Mater. 13 2003 85 88
8. A.W. Hofmann Proc. R. Soc. Lond. 8 1855 1 3
9. IUPAC Gold Book-Conjugated System second ed. 1997 Blackwell Scientific Publications Oxford
10. P.V.R. Schleyer Chem. Rev. 105 2005 3433 3435
11. J.L. Bredas, D. Beljonne, V. Coropceanu, and J. Cornil Chem. Rev. 104 2004 4971 5004
12. J.L. Bredas, J. Cornil, D. Beljonne, D. Santos, A. Donizetti, and S. Zhigang Acc. Chem. Res. 32 1999 267 276
13. J. Cornil, D.A. dosSantos, X. Crispin, R. Silbey, and J.L. Bredas J. Am. Chem. Soc. 120 1998 1289 1299
14. J.L. Bredas, and G.B. Street Acc. Chem. Res. 18 1985 309 315
15. A. Warshel, and M. Karplus J. Am. Chem. Soc. 96 1974 5677 5689
16. S.C. Yang, W. Graupner, S. Guha, P. Puschnig, C. Martin, H.R. Chandrasekhar, M. Chandrasekhar, G. Leising, C. Ambrosch, and U. Scherf Phys. Rev. Lett. 85 2000 2388 2391
17. W.F. Beadle, J.C.C. Tsai, and R.D. Plummer Quick Reference Manual for Semiconductor Engineers 1985 Wiley New York
18. C.C. Chu, G. Raffy, D. Ray, A.D. Guerzo, B. Kauffmann, G. Wantz, L. Hirsch, and D.M. Bassani J. Am. Chem. Soc. 132 2010 12717 12723
19. A.G.L. Olive, A.D. Guerzo, C. Belin, J. Reichwagen, H. Hopf, and J.P. Desvergne Res. Chem. Intermed. 34 2008 137 145
20. J.H. Park, D.S. Chung, J.W. Park, T. Ahn, H. Kong, Y.K. Jung, J. Lee, M.H. Yi, C.E. Park, S.K. Kwon, and H.K. Shim Org. Lett. 9 2007 2573 2576
21. M.M. Payne, S.R. Parkin, and J.E. Anthony J. Am. Chem. Soc. 127 2005 8028 8029
22. J.E. Anthony, D.L. Eaton, and S.R. Parkin Org. Lett. 4 2001 15 18
23. T. Hasegawa, and J. Takeya Sci. Technol. Adv. Mater. 10 2009 024314 024330
24. A. Hepp, H. Heil, W. Weise, M. Ahles, R. Schmechel, and H.V. Seggern Phys. Rev. Lett. 91 2003 157406 157409
25. C. Piliego, D. Jarzab, G. Gigli, Z. Chen, A. Facchetti, and M.A. Loi Adv. Mater. 21 2009 1573 1576
26. L.R. Domingo, and M.J. Aurell J. Org. Chem. 67 2002 959 965
27. A. Callegari, R. Pearman, S. Choi, P. Engels, H. Srivastava, M. Gruebele, K.K. Lehmann, and G. Scoles Mol. Phys. 101 2003 551 568
28. M.D. Su J. Comput. Chem. 31 2010 43 56
29. E.V. Canesi, G. Dassa, C. Botta, A. Bianco, C. Bertarelli, and G. Zerbi Open Chem. Phys. J. 1 2008 23 28
30. M. Ashizawa, T. Niimura, and Y. Yu Tetrahedron 68 2012 2790 2798
31. J.A. Letizia, A. Facchetti, C.L. Stern, M.A. Ratner, and T.J. Marks J. Am. Chem. Soc. 127 2005 13476 13477
32. H. Pang, P.J. Skabara, D.J. Crouch, W. Duffy, M. Heeney, I. McCulloch, S.J. Coles, P.N. Horton, and M.B. Hursthouse Macromolecules 40 2007 6585 6593
33. S. Mansouri, S. Zorai, and R. Bourguiga Synth. Met. 162 2012 231 235
34. B. Noda, H. Wada, K. Shibata, T. Yoshino, M. Katsuhara, I. Aoyagi, T. Mori, T. Taguchi, T. Kambayashi, K. Ishikawa, and H. Takezoe Nanotechnology 18 2007 424009 424019
35. X.K. Chen, L.Y. Zou, S. Huang, C.G. Min, A.M. Ren, J.K. Feng, and C.C. Sun Org. Electron. 12 2011 1198 1210
36. A. Irfan, M. Nadeem, M. Athar, F. Kanwal, and J. Zhang Comput. Theor. Chem. 968 2011 8 11
37. A. Irfan, A.G. Al-Sehemi, S. Muhammad, and J. Zhang Aust. J. Chem. 64 2011 1587 1592
38. M.S. Wrackmeyer, M. Heinn, A. Petrich, J. Meiss, M. Hummert, M.K. Riede, and K. Leo Sol. Energy Mater. Sol. Cells 95 2011 3171 3175
39. S. Das, S.P. Senanayak, A. Bedi, K.S. Narayan, and S.S. Zade Polymer 52 2011 5780 5787
40. J.A. Letizia, S. Cronin, R.P. Ortiz, A. Facchetti, M.A. Ratner, and T.J. Marks Chem. - Eur. J. 16 2010 1911 1928
41. F. Buonocore, and A. di Matteo Theor. Chem. Acc. 124 2009 217 223
42. Q.X. Wu, Y. Geng, Y. Liao, X.D. Tang, G.C. Yang, and Z.M. Su Theor. Chem. Acc. 131 2012 1121 1129
43. K.N.N. Unni, S.D. Seignon, and N.J. Michel J. Mater. Sci. 41 2006 317 322
44. P. Pingel, A. Zen, D. Neher, I. Lieberwirth, G. Wegner, S. Allard, and U. Scherf Appl. Phys. A 95 2009 67 72
45. A. Irfan, J. Zhang, and Y. Chang Theor. Chem. Acc. 127 2010 587 594
46. T.D. Anthopoulos, F.B. Kooistra, H.J. Wondergem, D. Kronholm, J.C. Hummelen, and D.M. Leeuw Adv. Mater. 18 2006 1679 1684
47. B.A. Jones, A. Facchetti, M.R. Wasielewski, and T.J. Marks Adv. Funct. Mater. 18 2008 1329 1339
48. H. Koezuka, A. Tsumura, and T. Ando Synth. Met. 18 1987 699 704
49. B.A. Jones, A. Facchetti, M.R. Wasielewski, and T.J. Marks J. Am. Chem. Soc. 129 2007 15259 15278
50. B.A. Jones, M.J. Ahrens, M.H. Yoon, A. Facchetti, T.J. Marks, and M.R. Wasielewski Angew. Chem., Int. Ed. 43 2004 6363 6366
51. Z.N. Bao, A.J. Lovinger, and J. Brown J. Am. Chem. Soc. 120 1998 207 208
52. M.Y. Kou, H.Y. Chen, and I. Chao Chem.Eur. J. 13 2007 4750 4758
53. M. Winkler, and K.N. Houk J. Am. Chem. Soc. 129 2007 1805 1815
54. E.J. Meijer, D.M. Leeuw, S. Setayesh, E. Veenendaal, B.H. Huisman, P.W.M. Blom, J.C. Hummelen, U. Scherf, and T.M. Klapwijk Nat. Mater. 2 2003 678 682
55. J. Wang, H.B. Wang, X.J. Yan, H.C. Huang, and D.H. Yan Chem. Phys. Lett. 407 2005 87 90
56. Y.X. Zhang, X. Cai, Y.Z. Ban, X.Y. Li, and J.Z. Jiang J. Phys. Chem. C 112 2008 5148 5159
57. M.L. Tang, A.D. Reichardt, N. Miyaki, R.M. Stoltenberg, and Z. Bao J. Am. Chem. Soc. 130 2008 6064 6065
58. S.W. Yin, Y.P. Yi, Q.X. Li, G. Yu, Y.Q. Liu, and Z.G. Shuai J. Phys. Chem. A 110 2006 7138 7143
59. M.L. Tang, J.H. Oh, A.D. Reichardt, and Z. Bao J. Am. Chem. Soc. 131 2009 3733 3740
60. S. Noro, T. Takenobu, Y. Iwasa, H.C. Chang, S. Kitagawa, T. Akutagawa, and T. Nakamura Adv. Mater. 20 2008 3399 3403
61. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
62. C. Lee, W. Yang, and R.G. Parr Phys. Rev. B 37 1988 785 789
63. P.J. Stephens, F.J. Devlin, C.F. Chabalowski, and M.J. Frisch J. Phys. Chem. 98 1994 11623 11627
64. Y.A. Duan, Y. Geng, H.B. Li, X.D. Tang, J.L. Jin, and Z.M. Su Org. Electron. 13 2012 1213 1222
65. R.C. Oliveira, and G.F. Bauerfeldt J. Chem. Phys. 137 2012 134306 134316
66. Q. Long, H. Ji, and L. Shushen Int. J. Quantum Chem. 109 2009 448 458
67. G.I. Csonka J. Mol. Struct. (Theochem) 584 2002 1 4
68. X. Zhao, Z. Zheng, S. Feng, Z. Shi, and D. Chen Int. J. Mol. Sci. 10 2009 3186 3193
69. M. Aghaie, M.H. Ghorbani, R. Fazaeli, and H. Aghaie J. Theor. Comput. Chem. 8 2009 765 772
70. S. Arulmozhi, M.V.A. Raj, and J. Madhavan Der Chemica Sinica 2 2011 158 163
71. K. Zhang, and A.C. Phillips J. Chem. Inf. Comput. Sci. 39 1999 382 395
72. R. Bauernschmitt, and R. Ahlrichs Chem. Phys. Lett. 256 1996 454 464
73. C.V. Caillie, and R.D. Amos Chem. Phys. Lett. 317 2000 159 164
74. F. Furche, and R. Ahlrichs J. Chem. Phys. 117 2002 7433 7447
75. G. Scalmani, M.J. Frisch, B. Mennucci, J. Tomasi, R. Cammi, and V. Barone J. Chem. Phys. 124 2006 1 15
76. J.E. Lee, G.C. Choi, N.G. Park, Y.K. Ha, and Y.S. Kim Curr. Appl. Phys. 4 2004 675 678
77. M.C. Zwier, J.M. Shorb, and B.P. Krueger J. Comput. Chem. 28 2007 1572 1581
78. E. Li, A. Kim, and L. Zhang J. Student Comput. Chem. 1 2007 1 7
79. E.V. Tsiper, Z.G. Soos, W. Gao, and A. Kahn Chem. Phys. Lett. 360 2002 47 52
80. Z.G. Soos, E.V. Tsiper, and A. Painelli J. Lumin. 110 2004 332 341
81. E.V. Tsiper, and Z.G. Soos Phys. Rev. B 68 2003 085301 085310
82. N.E. Gruhn, F.D.A. daSilva, T.G. Bill, M. Malagoli, V. Coropceanu, A. Kahn, and J.L. Bredas J. Am. Chem. Soc. 124 2002 7918
83. J.R. Reimers J. Chem. Phys. 115 2001 9103 9109
84. A. Irfan, R.H. Cui, and J.P. Zhang Theor. Chem. Acc. 122 2009 275 281
85. V. Coropceanu, T. Nakano, N.E. Gruhn, O. Kwon, T. Yade, K. Katsukawa, and J.L. Bredas J. Phys. Chem. B 110 2006 9482 9487
86. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, O. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, and D.J. Fox Gaussian 09, Revision A.02 2009 Gaussian, Inc Wallingford, CT
87. P. Puzari, R.S. Swathi, B. Sarkar, and S. Adhikari J. Chem. Phys. 123 2005 134317 134328
88. J.A. Merritt, and K.K. Innes Spectrochim. Acta 16 1960 945 953
89. http://www.chemistry.msu.edu.
90. E.J. Beiting, K.J. Zeringue, and R.E. Stickel Spectrochim. Acta 4lA 1985 1413 1418
91. The National Institute of Standards and Technology (NIST). http://webbook.nist.gov/cgi/.
92. I.B. Berlman Handbook of Fluorescence Spectra of Aromatic Molecules 1965 Academic Press New York
93. Computational Chemistry Comparison and Benchmark Database. http://ccbdb.nist.gov.
94. W.R. Dawson, and M.W. Windsor Fluorescence yields of aromatic compounds J. Phys. Chem. 72 1968 3251 3260
95. J.M. Dixon, M. Taniguchi, and J.S. Lindsey Photochem. Photobiol. 81 2005 212 213
96. F.H. Quina, and F.A. Carroll J. Am. Chem. Soc. 98 1976 6 9
97. Y. Zhang, X. Cai, and J. Jiang J. Phys. Chem. C 112 2008 14579 14588