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

doi:10.6023/cjoc1106081

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (01): 113-120.DOI: 10.6023/cjoc1106081 Previous Articles Next Articles

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5,10,15,20-四{对[3,5-二-(烷氧基)苯甲酰胺基]苯基}卟啉及其锌配合物的合成表征

连文慧, 孙园园, 王彬彬, 单凝, 于连香, 于苗, 师同顺

吉林大学化学学院长春 130021

收稿日期:2011-06-08 修回日期:2011-08-29 发布日期:2011-09-19
通讯作者: 师同顺 E-mail:shitongshun@jlu.edu.cn

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

Lian Wenhui, Sun Yuanyuan, Wang Binbin, Shan Ning, Yu Lianxiang, Yu Miao, Shi Tongshun

College of chemistry, Jilin University, Changchun 130021

Received:2011-06-08 Revised:2011-08-29 Published:2011-09-19
Contact: SHI Tong-Shun E-mail:shitongshun@jlu.edu.cn

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.

Key words: porphyrin, Zn complex, XPS, fluorescence, raman

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Lian Wenhui, Sun Yuanyuan, Wang Binbin, Shan Ning, Yu Lianxiang, Yu Miao, Shi Tongshun . Preparation and Characterization of 5,10,15,20-Tetra[4-(3,5-dialkoxybenzamide) phenyl]porphyrin and Their Zn Complexes[J]. Chin. J. Org. Chem., 2012, 32(01): 113-120.

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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.

5,10,15,20-四{对[3,5-二-(烷氧基)苯甲酰胺基]苯基}卟啉及其锌配合物的合成表征

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

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