Citation: LIU Shu-Juan, MA Ting-Chun, XU Wen-Juan, LIU Xiang-Mei, ZHAO Qiang, HUANG Yan-Qin, HUANG Wei. Optoelectronic Properties for Main Group Element-Bridged Ladder Compounds[J]. Acta Physico-Chimica Sinica doi: 10.3866/PKU.WHXB201208272 shu

Optoelectronic Properties for Main Group Element-Bridged Ladder Compounds

1.
Key Laboratory for Organic Electronics & Information Displays and Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications, Nanjing 210046, P. R. China

Received Date: 25 June 2012
Available Online: 27 August 2012
Fund Project: 国家重点基础研究发展计划(2009CB930601, 2012CB933301) (2009CB930601, 2012CB933301) 国家自然科学基金(21174064, 21171098) (21174064, 21171098) 教育部创新团队(IRT1148) (IRT1148) 江苏省国际合作计划-重点国别和地区研发合作项目(BZ2010043) (BZ2010043) 南京邮电大学基金(NY210029) (NY210029)

Ladder-type π-conjugated molecules with fully ring-fused structures have fascinating optoelectronic properties because the flattened π-conjugated framework can eliminate conformational disorder and effectively enhance π-conjugation. Their optoelectronic properties can be modified by incorporating main group elements into the ladder skeleton. Heteroatom-bridges not only stiffen the skeleton but also contribute to the electronic structure through orbital interaction between the main group elements and the π-conjugated skeleton. Herein, the structural, electronic, and optical properties of bisand tetrakis-bridged (C, Si or P-bridged) stilbene derivatives were investigated by density functional theory (DFT) and time-dependent DFT (TDDFT) to provide theoretical understanding and predictions for these compounds. The electronic structures of these π-conjugated skeletons could be tuned by the incorporated elements. Compared with bis-bridged analogs, tetrakis-bridged derivatives exhibited substantial red shifts in the absorption and shorter radiative lifetimes because of extended π-conjugation. In addition, the energy barrier for the injection and transport rates of the holes and electrons was evaluated using ionization potentials, electronic affinities, and reorganization energies (λ). Compared to bis-bridged analogs, tetrakis-bridged derivatives exhibit higher accepting abilities for both holes and electrons.
- Density functional theory,
- Electronic properties,
- Ladder-type molecules,
- Main group element,
- Photophysical property
1. [1]
  
  (1) Scherf, U. J. Mater. Chem. 1999, 9, 1853. doi: 10.1039/a900447e
2. [2]
  (2) Watson, M. D.; Fechtenkötter, A.; Müllen, K. Chem. Rev. 2001,101, 1267. doi: 10.1021/cr990322p
3. [3]
  (3) Bendikov, M.;Wudl, F. Chem. Rev. 2004, 104, 4891. doi: 10.1021/cr030666m
4. [4]
  (4) Anthony, J. E. Chem. Rev. 2006, 106, 5028. doi: 10.1021/cr050966z
5. [5]
  (5) Fukazawa, A.; Yamaguchi, S. Chem. Asian J. 2009, 4, 1386.doi: 10.1002/asia.v4:9
6. [6]
  (6) Zhao, Q.; Zhang, H.;Wakamiya, A.; Yamaguchi, S. Synthesis2009, 1, 127.
7. [7]
  (7) Li, D.; Zhang, H.;Wang, C.; Huang, S.; Guo, J.;Wang, Y.J. Mater. Chem. 2012, 22, 4319. doi: 10.1039/c1jm14606h
8. [8]
  (8) A u, T.; Kobayashi, J.; Kawashima, T. Chem. Eur. J. 2007, 13,8051. doi: 10.1002/(ISSN)1521-3765
9. [9]
  (9) Fukazawa, A.; Yamada, H.; Yamaguchi, S. Angew. Chem. Int. Edit. 2008, 47, 5582. doi: 10.1002/anie.v47:30
10. [10]
  (10) Matsuda, T.; Kadowaki, S.; ya, T.; Murakami, M. Org. Lett.2007, 9, 133. doi: 10.1021/ol062732n
11. [11]
  (11) Shimizu, M.; Mochida, K.; Asai, Y.; Yamatani, A.; Kaki, R.;Hiyama, T.; Nagai, N.; Yamagishi H.; Furutani, H. J. Mater. Chem. 2012, 22, 4337. doi: 10.1039/c2jm15173a
12. [12]
  (12) Yamaguchi, S.; Xu, C.; Tamao, K. J. Am. Chem. Soc. 2003, 125,13662. doi: 10.1021/ja038487+
13. [13]
  (13) Xu, C.; Yamada, H.;Wakamiya, A.; Yamaguchi, S.; Tamao, K.Macromolecules 2004, 37, 8978. doi: 10.1021/ma0486546
14. [14]
  (14) Mouri, K.;Wakamiya, A.; Yamada, H.; Kajiwara, T.;Yamaguchi, S. Org. Lett. 2007, 9, 93. doi: 10.1021/ol062615s
15. [15]
  (15) Xu, C.;Wakamiya, A.; Yamaguchi, S. J. Am. Chem. Soc. 2005,127, 1638. doi: 10.1021/ja042964m
16. [16]
  (16) Kaszynski, P.; Dougherty, D. A. J. Org. Chem. 1993, 58, 5209.doi: 10.1021/jo00071a034
17. [17]
  (17) Patil, S. A.; Scherf, U.; Kadashchuk, A. Adv. Funct. Mater. 2003,13, 609. doi: 10.1002/(ISSN)1616-3028
18. [18]
  (18) Wakim, S.; Bouchard, J.; Blouin, N.; Michaud, A.; Leclerc, M.Org. Lett. 2004, 6, 3413. doi: 10.1021/ol048543r
19. [19]
  (19) Kawaguchi, K.; Nakano, K.; Nozaki, K. J. Org. Chem. 2007, 72,5119. doi: 10.1021/jo070427p
20. [20]
  (20) Su, H. C.; Fadhel, O.; Yang, C. J.; Cho, T. Y.; Fave, C.; Hissler,M.;Wu, C. C.; Reau, R. J. Am. Chem. Soc. 2006, 128, 983. doi: 10.1021/ja0567182
21. [21]
  (21) Baumgartner, T.; Neumann, T.;Wirges, B. Angew. Chem. Int. Edit. 2004, 43, 6197. doi: 10.1002/(ISSN)1521-3773
22. [22]
  (22) Baumgartner, T.; Bergmans,W.; KmrpMti, T.; Neumann, T.;Nieger, M.; NyulMszi, L. Chem. Eur. J. 2005, 11, 4687. doi: 10.1002/(ISSN)1521-3765
23. [23]
  (23) Dienes, Y.; Durben, S.; KmrpMti, T.; Neumann, T.; Englert, U.;NyulMszi, L.; Baumgartner, T. Chem. Eur. J. 2007, 13, 7487.doi: 10.1002/(ISSN)1521-3765
24. [24]
  (24) Fukazawa, A.; Hara, M.; Okamoto, T.; Son, E.-C.; Xu, C.;Tamao, K.; Yamaguchi, S. Org. Lett. 2008, 10, 913. doi: 10.1021/ol7030608
25. [25]
  (25) Han, L. Z.;Wang, Z.; Hua, Y. J.; Ren, A. M.; Liu, Y. L.; Liu, P.J. Acta Chim. Sin. 2012, 70, 579. [韩立志, 王卓, 华英杰,任爱民, 刘艳玲, 刘朋军. 化学学报, 2012, 70, 579.] doi: 10.6023/A1106061
26. [26]
  (26) Chen, L. T.; Yan, Y.; Zhang, C.; Ma, C. A. Acta Chim. Sin. 2010,68, 2167. [陈丽涛, 严妍, 张诚, 马淳安. 化学学报,2010, 68, 2167.]
27. [27]
  (27) Sun, H. T.; Tian, X. H.; Yuan, Y. Z.; Sun, J. Y.; Sun, Z. R.; Zhuo,X. L. Acta Phys. -Chim. Sin. 2011, 27, 1847. [孙海涛, 田晓慧, 元以中, 孙金煜, 孙真荣, 卓小玲. 物理化学学报, 2011, 27,1847.] doi: 10.3866/PKU.WHXB20110840
28. [28]
  (28) Liu, X. J.; Lin, T.; Gao, S.W.; Ma, R.; Zhang, J. Y.; Cai, X. C.;Yang, L.; Teng, F. Acta Phys. -Chim. Sin. 2012, 28, 1337.[刘小君, 林涛, 高少伟, 马睿, 张晋悦, 蔡新晨, 杨磊,滕枫. 物理化学学报, 2012, 28, 1337.] doi: 10.3866/PKU.WHXB201204092
29. [29]
  (29) Yue, Y.; Xu, H. X.; Hao, Y. Y.; Xie, X. D.; Qu, L. T.;Wang, H.;Xu, B. S. Acta Phys. -Chim. Sin. 2012, 28, 1593. [岳岩, 许慧侠, 郝玉英, 解晓东, 屈丽桃, 王华, 许并社. 物理化学学报, 2012, 28, 1593.] doi: 10.3866/PKU.WHXB201204181
30. [30]
  (30) Wang, F. J.; Zhou, D. H.; Zuo, S. Y.; Cao, J. F.; Peng, X. J. Acta Phys. -Chim. Sin. 2012, 28, 1645. [王凤娇, 周丹红, 左士颖,曹建芳, 彭孝军. 物理化学学报, 2012, 28, 1645.] doi: 10.3866/PKU.WHXB201205083
31. [31]
  (31) Zhao, P.; Xu, L. C.; Ma, L. Acta Phys. -Chim. Sin. 2011, 27,2541. [赵平, 绪连彩, 马丽. 物理化学学报, 2011, 27,2541.] doi: 10.3866/PKU.WHXB20111021
32. [32]
  (32) Keruckas, J.; Lygaitis, R.; Simokaitiene, J.; Grazulevicius, J. V.;Jankauskas, V.; Sini, G. J. Mater. Chem. 2012, 22, 3015. doi: 10.1039/c2jm14387a
33. [33]
  (33) Shi, L. L.; Hong, B.; Guan,W.;Wu, Z. J.; Su, Z. M. J. Phys. Chem. A 2010, 114, 6559. doi: 10.1021/jp1010617
34. [34]
  (34) Liu, T.; Xia, B. H.; Zheng, Q. C.; Zhou, X.; Pan, Q. J.; Zhang,H. X. J. Comput. Chem. 2010, 31, 628.
35. [35]
  (35) Yin, J.; Chen, R. F.; Zhang, S. L.; Ling, Q. D.; Huang,W.J. Phys. Chem. A 2010, 114, 3655.
36. [36]
  (36) Liu, S. J.; Sun, S.;Wang, C. M.; Zhao, Q.; Sun, H. B.; Li, F. Y.;Fan, Q. L.; Huang,W. ChemPhysChem 2011, 12, 313. doi: 10.1002/cphc.v12.2
37. [37]
  (37) Marcus, R. A. J. Chem. Phys. 1956, 24, 966. doi: 10.1063/1.1742723
38. [38]
  (38) Kan, Y. H.;Wu, K.; Zhu, Y. L.; Hou, L. M.; Su, Z. M. Acta Phys. -Chim. Sin. 2010, 26, 1423. [阚玉和, 吴凯, 朱玉兰,侯丽梅, 苏忠民. 物理化学学报, 2010, 26, 1423.] doi: 10.3866/PKU.WHXB20100528
39. [39]
  (39) Sun, G. Y.; Li, H. B.; Geng, Y.; Duan, Y. A.; Tang, X. D.; Su, Z.M.; Zhou, Z. Y. Chem. J. Chin. Univ. 2012, 33, 794. [孙光延,李海斌, 耿允, 段雨爱, 汤肖丹, 苏忠民, 周子彦. 高等学校化学学报, 2012, 33, 794.]
40. [40]
  (40) Hutchison, G. R.; Ratner, M. A.; Marks, T. J. J. Am. Chem. Soc.2005, 127, 2339. doi: 10.1021/ja0461421
41. [41]
  (41) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al. Gaussian 03,Revision E.01; Gaussian Inc.:Wallingford, CT, 2004.
42. [42]
  (42) Lee, C.; Yang,W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. doi: 10.1103/PhysRevB.37.785
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