Citation: HU Bo, YAO Chan, WANG Qing-Wei, ZHANG Hao, YU Jian-Kang. Electronic, Optical and Charge Transport Properties of D-π-A-π-D Type Naphthalene-Based Derivatives[J]. Acta Physico-Chimica Sinica, ;2012, 28(07): 1651-1657. doi: 10.3866/PKU.WHXB201204194 shu

Electronic, Optical and Charge Transport Properties of D-π-A-π-D Type Naphthalene-Based Derivatives

HU Bo ^1,2, ,
YAO Chan ^1,2 ,
WANG Qing-Wei ^1,2 ,
ZHANG Hao ³ ,
YU Jian-Kang ^4,3

1.
1. Faculty of Chemistry, Jilin Normal University, Siping 136000, Jilin Province, P. R. China;
2. Key Laboratory of Preparation and Applications of Environmental Friendly Materials of Ministry of Education, Jilin Normal University, Siping 136000, Jilin Province, P. R. China;
3. State Key Laboratory of Theoretical and Computational Chemistry, Jilin University, Changchun 130023, P. R. China;
4. Institute of Applied Physics and Technology, The Foundation Department of Liaoning Technical University, Huludao 123000, Liaoning Province, P. R. China

Received Date: 30 December 2011
Available Online: 19 April 2012
Fund Project: 科学技术研究项目(2010142) (2010142)四平市科技发展计划(2010009)资助 (2010009)

A luminescent donor-π-bridge-acceptor-π-bridge-donor (D-π-A-π-D) type naphthalene-based derivative and its“CH”/N substituted derivatives have been designed and their electronic, optical, and charge transport properties were investigated using quantum chemical approaches. Our calculations have shown that changes in molecular structure lead to modifications in the electronic structure, resulting in a modulation of the electronic bandgap and hence of the optical properties. Remarkably, the calculated emission spectra can nearly cover the full UV-Vis spectrum (from 447.7 to 743.1 nm). Also, large Stokes shifts were observed, ranging from 106.1 to 222.4 nm, resulting from a more planar conformation of the excited state between the two adjacent units in the molecular backbone relative to the ground state. Calculated results also showed that the designed compounds could be used as hole transport materials in organic light-emitting diodes.
- Organic light-emitting diode,
- Naphthalene,
- “CH”/N substitution,
- Electronic property,
- Optical property,
- Reorganization energy
1. [1]
  
  (1) Li, Z. H.;Wong, M. S.; Fukutani, H.; Tao, Y. Chem. Mater.2005, 17, 5032. doi: 10.1021/cm051163v
2. [2]
  (2) Yoon, M. H.; Facchetti, A.; Stern, C. E.; Marks, T. J. J. Am. Chem. Soc. 2006, 128, 5792. doi: 10.1021/ja060016a
3. [3]
  (3) Li, Q.; Yu, J. S.; Li, L.; Jiang, Y. D.; Suo, F.; Zhan, X.W. Acta Phys. -Chim. Sin. 2008, 24, 133. [李青, 于军胜, 李璐,蒋亚东, 锁钒, 占肖卫. 物理化学学报, 2008, 24, 133.]doi: 10.3866/PKU.WHXB20080123
4. [4]
  (4) Tang, X. Q.; Yu, J. S.; Li, L.;Wang, J.; Jiang, Y. D. Acta Phys. -Chim. Sin. 2008, 24, 1012. [唐晓庆, 于军胜, 李璐,王军, 蒋亚东. 物理化学学报, 2008, 24, 1012.] doi: 10.3866/PKU.WHXB20080617
5. [5]
  (5) Guo, X.; Qin, C. J.; Cheng, Y. X.; Xie, Z. Y.; Geng, Y. H.; Jing,X. B.;Wang, F. S.;Wang, L. X. Adv. Mater. 2009, 21, 3682.doi: 10.1002/adma.200803734
6. [6]
  (6) Yu, X. H.; Ge, G. P.; Zhang, G. L.; Guo, H. Q. Acta Phys. -Chim. Sin. 2010, 26, 1184. [于晓航, 葛国平, 张国林, 郭海清. 物理化学学报, 2010, 26, 1184.] doi: 10.3866/PKU.WHXB20100442
7. [7]
  (7) Chen, S. F.; Deng, L. L.; Xie, J.; Peng, L.; Xie, L. H.; Fan, Q.L.; Huang,W. Adv. Mater. 2010, 22, 5227. doi: 10.1002/adma.201001167
8. [8]
  (8) Xiao, L. X.; Chen, Z. J.; Qu, B.; Luo, J. X.; Kong, S.; ng, Q.H.; Kido, J. J. Adv. Mater. 2011, 23, 926. doi: 10.1002/adma.201003128
9. [9]
  (9) Xiao, L. X.; Hu, S. Y.; Kong, S.; Chen, Z. J.; Qu, B.; ng, Q.H. Acta Phys. -Chim. Sin. 2011, 27, 977. [肖立新, 胡双元,孔胜, 陈志坚, 曲波, 龚旗煌. 物理化学学报, 2011, 27,977.] doi: 10.3866/PKU.WHXB20110325
10. [10]
  (10) Wang, J.; Zhang, F. J.; Xu, Z.;Wang, Y. S. Acta Phys. -Chim. Sin. 2012, 28, 949. [王健, 张福俊, 徐征, 王永生. 物理化学学报, 2012, 28, 949.] doi: 10.3866/PKU.WHXB201201163
11. [11]
  (11) Thomas, K. R. J.; Lin, J. T.; Velusamy, M.; Tao, Y. T.; Chuen, C.H. Adv. Funct. Mater. 2004, 14, 83. doi: 10.1002/adfm.200304486
12. [12]
  (12) Kato, S. I.; Matsumoto, T.; Shigeiwa, M.; rohmaru, H.;Maeda, S.; Ishi-i, T.; Mataka, S. Chem. Eur. J. 2006, 12, 2303.doi: 10.1002/chem.200500921
13. [13]
  (13) Gahungu, G.; Zhang, J. P. J. Phys. Chem. B 2005, 109, 17762.doi: 10.1021/jp052220a
14. [14]
  (14) Chen, C. H.; Shi, J. M. Coord. Chem. Rev. 1998, 171, 161. doi: 10.1016/S0010-8545(98)90027-3
15. [15]
  (15) Hu, B.; Zhang, J. P. Polymer 2009, 50, 6172. doi: 10.1016/j.polymer.2009.10.034
16. [16]
  (16) McWeeny, R.; Diercksen, G. J. Chem. Phys. 1968, 49, 4852.doi: 10.1063/1.1669970
17. [17]
  (17) (a) Roothaan, C. C. J. Rev. Mod. Phys. 1951, 23, 69.
18. [18]
  (b) Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571.doi: 10.1103/RevModPhys.23.69
19. [19]
  (18) Foresman, J. B.; Head- rdon, M.; Pople, J. A.; Frisch, M. J.J. Phys. Chem. 1992, 96, 135. doi: 10.1021/j100180a030
20. [20]
  (19) Parr, R. G.; Yang,W. Density Functional Theory of Atoms and Molecules; Oxford University Press: Oxford, 1989.
21. [21]
  (20) (a) Ernzerhof, M.; Scuseria, G. E. J. Chem. Phys. 1999, 110, 5029.
22. [22]
  (b) Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158.doi: 10.1063/1.478401
23. [23]
  (21) (a) Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218.
24. [24]
  (b) Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996,256, 454.
25. [25]
  (c) Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R.J. Chem. Phys. 1998, 108, 4439. doi: 10.1063/1.477483
26. [26]
  (22) (a) Hariharan, P. C.; Pople, J. A. Mol. Phys. 1974, 27, 209.
27. [27]
  (b) rdon, M. S. Chem. Phys. Lett. 1980, 76, 163.
28. [28]
  (c) Frisch, M. J.; Pople, J. A.; Binkley, J. S. J. Chem. Phys.1984, 80, 3265. doi: 10.1080/00268977400100171
29. [29]
  (23) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03, Revision B.03; Gaussian Inc.: Pittsburgh, PA, 2003.
30. [30]
  (24) O'Boyle, N. M.; Vos, J. G. Gauss Sum 0.8; Dublin CityUniversity: Dublin, 2004.
31. [31]
  (25) Hu, B.; Zhang, J. P.; Chen, Y. Eur. Polym. J. 2011, 47, 208. doi: 10.1016/j.eurpolymj.2010.12.001
32. [32]
  (26) (a) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B 1988, 37, 785.
33. [33]
  (b) Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M.J. J. Phys. Chem. 1994, 98, 11623.
34. [34]
  (c) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. doi: 10.1103/PhysRevB.37.785
35. [35]
  (27) Yanai, T.; Tew, D.; Handy, N. Chem. Phys. Lett. 2004, 393, 51.doi: 10.1016/j.cplett.2004.06.011
36. [36]
  (28) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 09, Revision A.02; Gaussian Inc.:Wallingford, CT, 2009.
37. [37]
  (29) Sun, M.; Niu, B.; Zhang, J. P. Computational and Theoretical Chemistry 2008, 862, 85.
38. [38]
  (30) Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc.2005, 127, 2339.
39. [39]
  (31) Mala li, M.; Brédas, J. L. Chem. Phys. Lett. 2000, 327, 13.doi: 10.1016/S0009-2614(00)00757-0
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