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
1. [1]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
2. [2]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
3. [3]
  Jingwen Wang , Minghao Wu , Xing Zuo , Yaofeng Yuan , Yahao Wang , Xiaoshun Zhou , Jianfeng Yan . Advances in the Application of Electrochemical Regulation in Investigating the Electron Transport Properties of Single-Molecule Junctions. University Chemistry, 2025, 40(3): 291-301. doi: 10.12461/PKU.DXHX202406023
4. [4]
  Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
5. [5]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie WANG . Theoretical calculation of selective adsorption and separation of CO₂ by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385
6. [6]
  Xiaoling LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271
7. [7]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
8. [8]
  Wenjie SHI , Fan LU , Mengwei CHEN , Jin WANG , Yingfeng HAN . Synthesis and host-guest properties of imidazolium-functionalized zirconium metal-organic cage. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 105-113. doi: 10.11862/CJIC.20240360
9. [9]
  Yaqin Zheng , Lian Zhuo , Meng Li , Chunying Rong . Enhancing Understanding of the Electronic Effect of Substituents on Benzene Rings Using Quantum Chemistry Calculations. University Chemistry, 2025, 40(3): 193-198. doi: 10.12461/PKU.DXHX202406119
10. [10]
  Zitong Chen , Zipei Su , Jiangfeng Qian . Aromatic Alkali Metal Reagents: Structures, Properties and Applications. University Chemistry, 2024, 39(8): 149-162. doi: 10.3866/PKU.DXHX202311054
11. [11]
  Xuan Zhou , Yi Fan , Zhuoqi Jiang , Zhipeng Li , Guowen Yuan , Laiying Zhang , Xu Hou . Liquid Gating Mechanism and Basic Properties Characterization: a New Experimental Design for Interface and Surface Properties in the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 113-120. doi: 10.12461/PKU.DXHX202407111
12. [12]
  Wei Li , Ze Chang , Meihui Yu , Ying Zhang . Curriculum Ideological and Political Design of Piezoelectricity Measurement Experiments of Coordination Compounds. University Chemistry, 2024, 39(2): 77-82. doi: 10.3866/PKU.DXHX202308004
13. [13]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
14. [14]
  Qingyang Cui , Feng Yu , Zirun Wang , Bangkun Jin , Wanqun Hu , Wan Li . From Jelly to Soft Matter: Preparation and Properties-Exploring of Different Kinds of Hydrogels. University Chemistry, 2024, 39(9): 338-348. doi: 10.3866/PKU.DXHX202309046
15. [15]
  Dongheng WANG , Si LI , Shuangquan ZANG . Construction of chiral alkynyl silver chains and modulation of chiral optical properties. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 131-140. doi: 10.11862/CJIC.20240379
16. [16]
  Chen LU , Qinlong HONG , Haixia ZHANG , Jian ZHANG . Syntheses, structures, and properties of copper-iodine cluster-based boron imidazolate framework materials. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 149-154. doi: 10.11862/CJIC.20240407
17. [17]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
18. [18]
  Peng ZHOU , Xiao CAI , Qingxiang MA , Xu LIU . Effects of Cu doping on the structure and optical properties of Au₁₁(dppf)₄Cl₂ nanocluster. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1254-1260. doi: 10.11862/CJIC.20240047
19. [19]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
20. [20]
  Zhiwen HUANG , Qi LIU , Jianping LANG . W/Cu/S cluster-based supramolecular macrocycles and their third-order nonlinear optical responses. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 79-87. doi: 10.11862/CJIC.20240184

Get Citation

PDF

XML

Metrics

PDF Downloads(739)
Abstract views(1977)
HTML views(8)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142