D-<em>π</em>-A-<em>π</em>-D型萘基衍生物的电子、光谱和电荷传输性质

引用本文: 胡波, 姚婵, 王庆伟, 张浩, 于健康. D-π-A-π-D型萘基衍生物的电子、光谱和电荷传输性质[J]. 物理化学学报, 2012, 28(07): 1651-1657. doi: 10.3866/PKU.WHXB201204194 shu

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

D-π-A-π-D型萘基衍生物的电子、光谱和电荷传输性质

基金项目:
吉林省教育厅&ldquo

十一五&rdquo

科学技术研究项目(2010142) (2010142)

四平市科技发展计划(2010009)资助 (2010009)

摘要:

采用量子化学方法研究了给体-π桥-受体-π桥-给体(D-π-A-π-D)型萘基衍生物及其“CH”/N 杂原子取代衍生物的电子、光谱和电荷传输性质. 计算结果表明, 分子结构的变化引起了电子结构和能隙的变化, 进而改变了吸收和发射光谱. 其中, 衍生物的最大发射波长几乎覆盖了可见光区域(447.7-743.1 nm). 而且, 光谱的Stokes 位移较大(106.1-222.4 nm), 产生的原因在于, 与基态结构相比较, 衍生物的激发态结构中分子主干存在两个相连部分更为平面的构型. 计算结果还显示, 所有衍生物都可以作为有机电致发光二极管中的空穴传输材料.

关键词:

English

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

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: 07 June 2012
Fund Project:
吉林省教育厅&ldquo

十一五&rdquo

科学技术研究项目(2010142)

四平市科技发展计划(2010009)资助

Abstract:

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.

Key words:

1. [1]
  
  (1) Li, Z. H.;Wong, M. S.; Fukutani, H.; Tao, Y. Chem. Mater.2005, 17, 5032. doi: 10.1021/cm051163v
  (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(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(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(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(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(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(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(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(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(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(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(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(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(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(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(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.(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(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(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.(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.(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(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.(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.(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(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.(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.(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(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.(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.(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(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.(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.(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(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(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.(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.(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.(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
  (31) Mala li, M.; Brédas, J. L. Chem. Phys. Lett. 2000, 327, 13.doi: 10.1016/S0009-2614(00)00757-0

扫一扫看文章

计量

PDF下载量: 739
文章访问数: 2198
HTML全文浏览量: 17

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

D-π-A-π-D型萘基衍生物的电子、光谱和电荷传输性质

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

D-π-A-π-D型萘基衍生物的电子、光谱和电荷传输性质

English

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

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs