Citation: ZHAO Ping, XU Lian-Cai, MA Li. Spectral Research into Intramolecular Photoinduced Electron Transfer of Porphyrin-Anthraquinone Hybrids[J]. Acta Physico-Chimica Sinica, ;2011, 27(11): 2541-2546. doi: 10.3866/PKU.WHXB20111021 shu

Spectral Research into Intramolecular Photoinduced Electron Transfer of Porphyrin-Anthraquinone Hybrids

ZHAO Ping ^1, ,
XU Lian-Cai ² ,
MA Li ³

1.
1. School of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528458, Guangdong Province, P. R. China;
2. School of Material and Chemical Engineering, Zhengzhou University of Light Industry, Zhengzhou 450002, P. R. China;
3. College of Chemistry and Chemical Engineering, Henan University of Technology, Zhengzhou 450001, P. R. China

Received Date: 29 July 2011
Available Online: 19 August 2011
Fund Project: 广东省医学科研项目(B2010158)资助 (B2010158)

A series of covalently linked porphyrin (Por)-anthraquinone (AQ) hybrids Por-C_n-AQ (n=1, 4, 10) with flexible different length carbon chains were synthesized and their intramolecular photoinduced electron transfer (PET) properties were investigated mainly by steady-state fluorescence and decayed luminescence spectra. We studied the PET mechanism using density functional theory (DFT). We found that PET occurs from the porphyrin moiety to the anthraquinone moiety of these dyads and that the PET efficiency is influenced considerably by the length of the linkage between the two moieties in the hybrids. From both the experimental and theoretical results, we can conclude that the PET of these dyads is seemingly most compatible with a“through-bond”(super-exchange) mechanism.
- Porphyrin-anthraquinone dyad,
- Electron transfer,
- Fluorescence spectrum,
- Density functional theory
1. [1]
  (1) Adriana, A. R. M.;Walderez, G.; Mauro, C. G.; Márcia, A. S. Int. Biodeter. Biodegr. 2011, 65, 423.
2. [2]
  (2) Nathan, C.; Kerry, B. B.; Zhou, X. J.; Samuel, J. L.; Keith, C. G.; Timothy,W. J.; Paul, C. D.;Warwick, J. B. Sol. Energy Mater. Sol. Cells 2011, 95, 1767.
3. [3]
  (3) Bhattacharya, S.; Nayak, S. K.; Chattopadhyay, S.; Saha, D. J. Mol. Liq. 2008, 143, 125.
4. [4]
  (4) Hirakawa, K.; Segawa, H. J. Photochem. Photobiol. A 2010, 213, 73.
5. [5]
  (5) Tao, M. L.; Liu, L. Z.; Liu, D. Z.; Zhou, X. Q. Dyes Pigm. 2010, 85, 21.
6. [6]
  (6) Odobel, F.; Fortage, J. C. R. Chim. 2009, 12, 437.
7. [7]
  (7) Shibano, Y.; Sasaki, M.; Tsuji, H.; Araki, Y.; Ito, O.; Tamao, K. J. Organomet. Chem. 2007, 692, 356.
8. [8]
  (8) Durmus, M.; Chen, J. Y.; Zhao, Z. X.; Nyokong, T. Spectrochim. Acta A 2008, 70, 42.
9. [9]
  (9) Poon, C. T.; Zhao, S. S.;Wong,W. K.; Kwong, D.W. J. Tetrahedron Lett. 2010, 51, 664.
10. [10]
  (10) Zhao, J.W.; Liu, H. M.; Ni,W. B.; Guo, Y.; Yin, X. Acta Phys. -Chim. Sin. 2009, 25, 1472.
11. [11]
  [赵健伟, 刘洪梅, 倪文彬, 郭彦, 尹星. 物理化学学报, 2009, 25, 1472.]
12. [12]
  (11) Ren, X. F.; Ren, A. M.;Wang, Q.; Feng, J. K. Acta Phys. -Chim. Sin. 2010, 26, 110.
13. [13]
  [任雪峰, 任爱民, 王钦, 封继康. 物理化学学报, 2010, 26, 110.]
14. [14]
  (12) Liu, J.; Huang, J.W.; Shen, H.;Wang, H.; Yu, H. C.; Ji, L. N. Dyes Pigm. 2008, 77, 374.
15. [15]
  (13) Miao, D.; Xu, Y. Z.; Yang, J.; Xu, Z. H. Spectrochim. Acta A 2004, 24, 513.
16. [16]
  [苗笛, 徐怡庄, 杨军, 许振华. 光谱学与光谱分析, 2004, 24, 513.]
17. [17]
  (14) Perun, S.; Tatchen, J.; Marian, C. M. Chem. Phys. Chem. 2008, 9, 282.
18. [18]
  (15) Li, C.; Zhang, L.; Zhang, C.; Hirao, H.;Wu,W.; Shaik, S. Angew. Chem. Int. Edit. 2007, 46, 8168.
19. [19]
  (16) Zhang, X.; Muranaka, A.; Lu,W.; Zhang, Y.; Bian, Y.; Jiang, J.; Kobayashi, N. Chem. Eur. J. 2008, 14, 4667.
20. [20]
  (17) Zhang, Y. H.; Ruan,W. J.;Wu, Y. Acta Phys. -Chim. Sin. 2005, 21, 1390.
21. [21]
  [章应辉, 阮文娟, 吴扬. 物理化学学报, 2005, 21, 1390.]
22. [22]
  (18) Becke, A. D. J. Chem. Phys. 1993, 98, 5648.
23. [23]
  (19) Rassolov, V. A.; Pople, J. A.; Ratner, M. A.;Windus, T. L. J. Chem. Phys. 1998, 109, 1223.
24. [24]
  (20) Zhurko, G. A.; Zhurko, D. A. Chemcraft, Version 1.6; Plimus, Inc.: Milpitas, USA, 2011.
25. [25]
  (21) Frisch, M. J.; Trucks, G.W.; Schlegel, H. B.; et al . Gaussian 03, Revision D.01; Gaussian Inc.:Wallingford, CT, 2004.
26. [26]
  (22) Huang, J.W.; Ji, L. N. Chem. J. Chin. Univ. 1995, 16, 163.
27. [27]
  [黄锦汪, 计亮年. 高等学校化学学报, 1995, 16, 163.]
28. [28]
  (23) Maza,W. A.; Larsen, R.W. Biophys. J. 2010, 98, 565.
29. [29]
  (24) Hutchison, J. A.; Bell, T. D. M.; Ganguly, T.; Ghiggino, K. P.; Langford, S. J.; Lokan, N. R.; Paddon-Row, M. N. J. Photochem. Photobiol. A 2008, 197, 220.
30. [30]
  (25) Karr, P. A.; Zandler, M. E.; Beck, M.; Jaeger, J. D.; McCarty, A. L.; Smith, P. M.; D'Souza, F. J. Mol. Struct. 2006, 765, 91.
31. [31]
  (26) Le, X. Y.; Ji, L. N.;Wu, F. H.; Song, F. Y. Chin. Sci. Bull. 1997, 42, 1103.
32. [32]
  [乐学义, 计亮年, 毋福海, 宋粉云. 科学通报. 1997, 42, 1103.]
33. [33]
  (27) Le, X. Y.; Ji, L. N. Chin. Sci. Bull. 2001, 46, 1235.
34. [34]
  [乐学义, 计亮年. 科学通报, 2001, 46, 1235.]
35. [35]
  (28) Ren, Q. Z.; Huang, J.W.; Lin, C. Y.; Ji, L. N. Chem. J. Chin. Univ. 1999, 20, 333.
36. [36]
  [任奇志, 黄锦汪, 林翠梧, 计亮年. 高等学校化学学报, 1999, 20, 333.]
37. [37]
  (29) Kuznetaov, A. M.; Ulstrup, J. J. Chem. Phys. 1981, 75, 2074.
38. [38]
  (30) Warman, J. M. Nature 1986, 320, 615.
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