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]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  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
10. [10]
  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
11. [11]
  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
12. [12]
  Xin MA , Ya SUN , Na SUN , Qian KANG , Jiajia ZHANG , Ruitao ZHU , Xiaoli GAO . A Tb₂ complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357
13. [13]
  Zhaoyang WANG , Chun YANG , Yaoyao Song , Na HAN , Xiaomeng LIU , Qinglun WANG . Lanthanide(Ⅲ) complexes derived from 4′-(2-pyridyl)-2, 2′∶6′, 2″-terpyridine: Crystal structures, fluorescent and magnetic properties. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1442-1451. doi: 10.11862/CJIC.20240114
14. [14]
  Daojuan Cheng , Fang Fang . Exploration and Implementation of Science-Education Integration in Organic Chemistry Teaching for Pharmacy Majors: A Case Study on Nucleophilic Substitution Reactions of Alkyl Halides. University Chemistry, 2024, 39(11): 72-78. doi: 10.12461/PKU.DXHX202403105
15. [15]
  Laiying Zhang , Yinghuan Wu , Yazi Yu , Yecheng Xu , Haojie Zhang , Weitai Wu . Innovation and Practice of Polymer Chemistry Experiment Teaching for Non-Polymer Major Students of Chemistry: Taking the Synthesis, Solution Property, Optical Performance and Application of Thermo-Sensitive Polymers as an Example. University Chemistry, 2024, 39(4): 213-220. doi: 10.3866/PKU.DXHX202310126
16. [16]
  Wentao Lin , Wenfeng Wang , Yaofeng Yuan , Chunfa Xu . Concerted Nucleophilic Aromatic Substitution Reactions. University Chemistry, 2024, 39(6): 226-230. doi: 10.3866/PKU.DXHX202310095
17. [17]
  Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C₃N₄/Ti₃C₂T_x Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
18. [18]
  Liang MA , Honghua ZHANG , Weilu ZHENG , Aoqi YOU , Zhiyong OUYANG , Junjiang CAO . Construction of highly ordered ZIF-8/Au nanocomposite structure arrays and application of surface-enhanced Raman spectroscopy. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1743-1754. doi: 10.11862/CJIC.20240075
19. [19]
  Tengjiao Wang , Tian Cheng , Rongjun Liu , Zeyi Wang , Yuxuan Qiao , An Wang , Peng Li . Conductive Hydrogel-based Flexible Electronic System: Innovative Experimental Design in Flexible Electronics. University Chemistry, 2024, 39(4): 286-295. doi: 10.3866/PKU.DXHX202309094
20. [20]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373

Get Citation

PDF

XML

Metrics

PDF Downloads(739)
Abstract views(1893)
HTML views(6)

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