Citation: ZHANG Xiao-Hong, GUO Hong-Rui, JIAO Zhi, YAN Wei-Wei, RUAN Wen-Juan, ZHU Zhi-Ang. Weak Interactions in Asymmetric Porphyrin Systems[J]. Acta Physico-Chimica Sinica, ;2011, 27(04): 774-780. doi: 10.3866/PKU.WHXB20110432 shu

Weak Interactions in Asymmetric Porphyrin Systems

1.
College of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received Date: 27 December 2010
Available Online: 14 March 2011
Fund Project: 国家自然科学基金(20671053)资助项目 (20671053)

The weak interactions of 5-imidazolylmethylphenyl-10,15,20-tri-tert-butylphenylporphyrin (1) and 5-imidazolylmethylphenyl-10,15,20-triphenylporphyrin (2) were investigated in chloroform by ¹H NMR, UV-Vis and fluorescence spectroscopies, and molecular modeling simulation. The ¹H NMR chemical shifts of imidazole in compounds 1 and 2 move upfield compared with that of free imidazole and this shows that intramolecular or intermolecular weak interactions exist in both compounds. Compared with the UV-Vis spectra of compounds 1 and 2 in acetone, their spectra in chloroform show a split Soret band for compound 1, which indicates a weak intramolecular interaction and a red shift of 27 nm for compound 2, which also suggests a weak intermolecular interaction. The fluorescence data supports these results and the data obtained from the molecular simulation are consistent with those of the spectral analyses.
- Weak interaction,
- Asymmetric porphyrin,
- ¹H NMR,
- UV-Vis spectrum,
- Conformation analysis
1. [1]
  
  (1) Lehn, J. M. Angew. Chem. Int. Edit. 1990, 29, 1304.
2. [2]
  (2) Okamura, M. Y.; Feher, G.; Nelson, N. Photosynthesis; vindjee: New York, 1982; p 195.
3. [3]
  (3) Crossley, M. J.; Burn, P. L. Chem. Commun. 1991, 1569.
4. [4]
  (4) Tsuda, A.; Osuka, A. Science 2001, 293, 79.
5. [5]
  (5) Imahori, H. J. Phys. Chem. B 2004, 108, 6130.
6. [6]
  (6) Maruo, N.; Uchiyama, M.; Kato, T.; Arai, T.; Akisada, H.; Nishino, N. Chem. Commun. 1999, 2057.
7. [7]
  (7) Ogawa, K.; Kobuke, Y. Angew. Chem. Int. Edit. 2000, 39, 4070.
8. [8]
  (8) Balaban, T. S. Accounts. Chem. Res. 2005, 38, 612.
9. [9]
  (9) Drain, C. M.; ldberg, I.; Sylvain, I.; Falber, A. Top. Curr. Chem. 2005, 245, 55.
10. [10]
  (10) Elemans, J. A. A. W.; Hameren, R.; Nolte, R. J. M.; Rowan, A. E. Adv. Mater. 2006, 18, 1251.
11. [11]
  (11) Shi, S. Q.; Yang, G. Y.; Hao, Z. F.; Pan, C. F. ChemOnline 2001, 6, 63.
12. [12]
  [石双群, 杨国营, 郝振芳, 潘成福. 化学通报, 2001, 6, 63.]
13. [13]
  (12) Furutsu, D.; Satake, A.; Kobuke, Y. Inorg. Chem. 2005, 44, 4460.
14. [14]
  (13) Takahashi, R. A.; Kobuke, Y. J. Am. Chem. Soc. 2003, 125, 2372.
15. [15]
  (14) Hajjaj, F.; Yoon, Z. S.; Yoon, M. C.; Park, J.; Satake, A.; Kim, D.; Kobuke, Y. J. Am. Chem. Soc. 2006, 128, 4612.
16. [16]
  (15) Ruan, W. J.; Zhang, Y. L.; Zhao, X. J.; Jiang, D. Q.; Zhu, Z. A. Chem. J. Chin. Univ. 2003, 24, 1657.
17. [17]
  [阮文娟, 张玉玲, 赵, 江冬青, 朱志昂. 高等学校化学学报, 2003, 24, 1657.]
18. [18]
  (16) Yu, Q. S.; Zhu, L. G. Molecular Design; Higher Education Press: Beijing, 2000; p 7.
19. [19]
  [俞庆森, 朱龙观. 分子设计导论. 北京: 高等教育出版社, 2000: 7.]
20. [20]
  (17) Perrin, D. D.; Armare , W. L. F.; Perrin, D. R. Purification of Laboratory Chemicals, 2nd ed.; Chemical Laboratory Press: Beijing, 1987; p 126; translated by Shi, Y.
21. [21]
  [Perrin, D. D.; Armare , W. L. F.; Perrin, D. R. 实验室化学药品的提纯, 第二版. 时雨, 译. 北京: 化学工业出版社, 1987: 126.]
22. [22]
  (18) Jasinski, S.; Ermilov, E. A.; Jux, N.; Röder, B. Eur. J. Org. Chem. 2007, 7, 1075.
23. [23]
  (19) Tome, J. P. C.; Neves, M. G. P. M. S.; Tome, A. C. Bioorg. Med. Chem. 2005, 13, 3878.
24. [24]
  (20) Hu, S. G.; Huang, J. J.; Ma, L.; Luo, H. Y.; Ji, L. N. Spectroscopy and Spectral Analysis 2004, 24, 381.
25. [25]
  [胡曙光, 黄锦汪, 马丽, 罗海英, 计亮年. 光谱与光谱分析, 2004, 24, 381.]
26. [26]
  (21) Johannes, M. K.; Ernst, R. S. J. Langmuir 1995, 11, 214.
27. [27]
  (22) Schenning, A. P. H. J.; Benneker, F. B. G.; Geurts, H. P. M.; Liu, X. Y.; Nolte, R. J. M. J. Am. Chem. Soc. 1996, 118, 8549.
28. [28]
  (23) Zou, X. P.; Hu, Z. Z.; Chen, R. Journal of Instrumental Analysis 2006, 25, 81.
29. [29]
  [邹欣平, 胡珍珠, 陈然. 分析测试学报, 2006, 25, 81.]
30. [30]
  (24) Zhao, H. Q.; Chen, D. M. Chin. J. Spectr. Lab. 2000, 17, 257.
31. [31]
  [赵慧卿, 陈东明. 光谱实验室, 2000, 17, 257.]
32. [32]
  (25) Zhang, G. W.; Fan, Q. L.; Huang, W. Chem. J. Chin. Univ. 2009, 30, 413.
33. [33]
  [张广维, 范曲立, 黄维. 高等学校化学学报, 2009, 30, 413.]
34. [34]
  (26) Ruan, W. J.; Zhu, Z. A. Chin. J. Struct. Chem. 1998, 17, 159.
35. [35]
  [阮文娟, 朱志昂. 结构化学, 1998, 17, 159.]
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