Articles

Preparation and Characterization of 5,10,15,20-Tetra[4-(3,5-dialkoxybenzamide) phenyl]porphyrin and Their Zn Complexes

  • LIAN Wen-Hui ,
  • SUN Yuan-Yuan ,
  • WANG Bin-Bin ,
  • DAN Ning ,
  • YU Lian-Xiang ,
  • YU Miao ,
  • SHI Tong-Shun
Expand
  • College of chemistry, Jilin University, Changchun 130021

Received date: 2011-06-08

  Revised date: 2011-08-29

  Online published: 2011-09-19

Abstract

In this paper, five novel 5,10,15,20-tetra[4-(3,5-dialkoxybenzamide)phenyl]porphyrin ligands and their Zn complexes were synthesized and characterized by means of IR, UV-Vis, 1H NMR, elemental analysis and XPS. Raman and fluorescence spectra of the ten amide group porphyrin ligands and Zn complexes were investigated. The results show that the length of side chains does not have evident effect on the Raman spectra and fluorescence spectra of porphyrin compounds, their substituent effect is basically the same. The fluorescence intensity of porphyrin ligands was stronger than that of Zn complexes. In the Raman spectra, there were much difference between the porphyrin ligands and Zn complexes due to changes of the symmetry of porphyrin plane and electron effect of the d orbits of the zinc ion.

Cite this article

LIAN Wen-Hui , SUN Yuan-Yuan , WANG Bin-Bin , DAN Ning , YU Lian-Xiang , YU Miao , SHI Tong-Shun . Preparation and Characterization of 5,10,15,20-Tetra[4-(3,5-dialkoxybenzamide) phenyl]porphyrin and Their Zn Complexes[J]. Chinese Journal of Organic Chemistry, 2012 , 32(01) : 113 -120 . DOI: 10.6023/cjoc1106081

References

[1] Smith, K. M. Porphyrins and Metalloporphyrins, Amsterdan, Elsevier, 1975.

[2] Lammi, R. K.; Ambroise, A.; Balasubramanian, T.; Wagner, R. W.; Bocian, D. F.; Holten, D.; Lindsey, J. S.; J. Am. Chem. Soc. 2000, 122, 7579.

[3] Sternberg, E. D.; Dolphin, D.; Bruckner, C. Tetrahedron 1998, 54, 4151.

[4] Li, J.; Ambroise, A.; Yang, S. I. J. Am. Chem. Soc. 1999, 121, 8927.

[5] Anderson, H. L. Chem. Commun. 1999, 23, 2323.

[6] Burroughes, H.; Bradley, D. C.; Brown, A. R.; Parker, L. D. Nature 1990, 347, 539.

[7] (a) Ohtake, T.; Ogasawara, M.; Ito-Akita, K.; Nishina, N.; Ujiie, S.; Ohno, H. Chem. Mater. 2000, 12, 782. (b) Percec, V.; Johansson, G.; Ungar, G.; Zhou, J. J. Am. Chem. Soc. 1996, 118, 9855. (c) Lehmann, M.; Gearba, R. I.; Koch, M. H. J.; Ivanov, D. A.Chem. Mater. 2004, 16, 374.

[8] Zhu, B. K.; Xu, Z. K. ; Xu, Y. Y. Chin. J. Appl. Chem. 1999, 16(1), 68 (in Chinese). (朱宝库, 徐志康, 徐又一, 应用化学, 1999, 16(1), 68.)

[9] Wang, D. J.; Zhang, J.; Shi, T. S.; Wang, B. H. J. Photochem. Photobiol. A 1996, 93, 21.

[10] Horrocks Jr, W. D.; Wong, C.-P. J. Am. Chem. Soc. 1976, 98, 7157.

[11] Liu, W.; Shi, Y. H.; Shi, T. S. Chem. J. Chin. Univ. 2003, 24, 200.

[12] Maaon, S. F. J. Am. Chem. Soc. 1958, 976.

[13] Gouterman, M. J. Mol. Spectrosc. 1961, 6, 138

[14] Luo, G. T.; Xu, Q. B.; Chen, Z. X.; Teng, L. L. Chin. J. Org. Chem. 2009, 29, 9 (in Chinese). (罗国添, 徐庆兵, 陈治希, 滕莉丽, 有机化学, 2009, 29, 9.)

[15] Jiang, Y. S.; Li, T. J. Photochemistry, Chemical Industry Press, Beijing, 2005 (in Chinese). (姜月顺, 李铁津, 光化学, 化学工业出版社, 2005.)

[16] Chen, G. Z.; Huang, X. Z.; Zheng, Z. Z.; Xu, J. G.; Wang, Z. B.; Fluorometric Determination, Science Press, Beijing, 1990 (in Chinese). (陈国珍, 黄贤智, 郑朱梓, 许金钩, 王尊本, 荧光分析法, 科学 出版社, 北京, 1990.)

[17] Falk, E. Porphyrins and Metalloporphyrin, Elsevier, Amsterdan, 1964, p. 55.

[18] Gottfried, J. M.; Flechtner, K.; Kretschmann, A.; Lukasczyk, T.; Steinruck, H. P. J. Am. Chem. Soc. 2006, 128, 5644.

[19] Wagner, C. D.; Riggs, W. M.; Davis, L. E.; Moulder, J. F.; Muilenberg, G. E. Handbook of X-ray Photoelectron Spectroscopy, Perkin-Elmer Corporation, New York, 1979.
Outlines

/