Synthesis and Electrochemical Properties of Tetra (p-formylester-ferrocene-3-ethoxyphenyl) phenylporphyrin

doi:10.7503/cjcu20130360

Abstract

Abstract:

Porphyrins have received the considerable attention because of their electron-transfer processes, photo-physics, biological processes and catalytic behaviors. This rapid development derives from their strong delocalization of π electron and conjugated macrocycles. The control of orientation of porphyrin chromophores can play a very important role. The functions of materials are related to the molecular alignments as well as the molecular structures. There were a number of reports on tetraphenylporphyrin derivatives, but those bearing the meso-substituted p-formyl-ferrocene group have been studied very little. In this paper, a symmetrical porphyrin with p-formyl-ferrocene group tetra(p-formylester-ferrocene-3-ethoxyphenyl)phenylporphyrin, was designed and synthesized through tetra(4-hydroxy-3-ethoxyphenal) porphyrin and formyl-ferrocene in CH₂Cl₂. The structure of tetra(p-formylester-ferrocene-3-ethoxyphenyl) phenylporphyrin was confirmed by UV-Vis, IR and ¹H NMR spectra. The UV-Vis absorption and fluorescence spectra indicated weak electronic interaction in ground state and strong electronic interaction in excited state between the ferrocene donors and the porphyrin acceptors. The cyclic voltammetry indicated that ferrocene substituents have a significant effect on the redox potentials.

Key words: Tetra(p-formylester-ferrocene-3-ethoxyphenyl)phenylporphyrin, Formyl-ferrocene, Electroche-mistry

CLC Number:

O614

TrendMD:

WANG Ying, ZHANG Jia-Yan, ZHENG Zhi-Feng, ZHUANG Chang-Fu, LEI Fu-Hou. Synthesis and Electrochemical Properties of Tetra (p-formylester-ferrocene-3-ethoxyphenyl) phenylporphyrin[J]. Chem. J. Chinese Universities, 2013, 34(9): 2051.

References

[1] Li G., Bhosale S. V., Wang T., Hackbarth S., Roeder B., Siggel U., Fuhrhop J. H., J. Am. Chem. Soc., 2003, 125, 10693—10702

[2] Guo X. M., Guo B., Zhang Q. Y., Sun X. M., Dalton Trans., 2011, 40, 3039—3046

[3] Shan N., Lian W. H., Wang B. B., Sun Y. Y., Zheng W. Q., Yu M., Shi T. S., Chem. J. Chinese Universities, 2011, 32(12), 2733—2738(单凝, 连文慧, 王彬彬, 孙园园, 郑文琦, 于苗, 师同顺. 高等学校化学学报, 2011, 32(12), 2733—2738)

[4] Wasielewski M. R., Chem. Rev., 1992, 92, 435—461

[5] Chcng K. L., Li H. W., Ng D. K., Organomet. Chem., 2004, 689, 1593—1598

[6] Souza F., Ito O., Coord. Chem. Rev., 2005, 249, 1410—1422

[7] Health J. R., Kuekes P. J., Snider G. S., Williams R. S., Science, 1998, 280, 1716—1721

[8] Gust D., Moore T. A., Moore A. L., Acc. Chem. Res., 1993, 26, 198—205

[9] Liu Z., Yasseri A. A., Lindsey J. S., Bocian D. F., Science, 2003, 302, 1543—1545

[10] Chen Y., Jung J., Ohlberg D., Li X., Stewart D. R., Jeppesen K. A., Stoddart J. F., Williams R. S., Nanotechnology, 2003, 14, 462—468

[11] Guo X. M., Guo B., Shi T. S., Inorg. Chim. Acta, 2010, 363(2), 317—323

[12] Olivier L., Daniele D., Christian B., Christophe L., Alain R., Marion H., Helene C., Nicole M., Nicole B., J. Med. Chem., 2000, 43, 2285—2289

[13] Zhu J. L., Zhang X. F., Fang Y. Y., Sun B., Lu G. F., Ou Z. P., Chinese J. Inorg. Chem., 2013, 29(1), 199—205(朱佳丽, 张秀风, 房媛媛, 孙斌, 路桂芬, 欧忠平. 无机化学学报, 2013, 29(1), 199—205)

[14] Guo X. M., Su L. J., Yu L. X., Shi T. S., Chem. J. Chinese Universities, 2006, 27(3), 410—413(郭喜明, 苏连江, 于莲香, 师同顺. 高等学校化学学报, 2006, 27(3), 410—413)

[15] Liu W., Shi Y. H., Wang Y. J., Chem. J. Chinese Universities, 2003, 24(2), 200—204(柳巍, 师宇华, 王银杰. 高等学校化学学报, 2003, 24(2), 200—204)

[16] Guo X. M., Guo B., Sun X. M., Zhang Q. Y., Shi T. S., Chin. J. Chem., 2011, 29(2), 363—368

[17] Sun E. J., Wang D., Cheng X. L., Shi Y. H., Shi T. S., Chem. J. Chinese Universities, 2007, 28(7), 1208—1213(孙二军, 王栋, 程秀利, 师宇华, 师同顺. 高等学校化学学报, 2007, 28(7), 1208—1213)

[18] Gentemann S., Medforth C. J., Forsyth T. P., Nurco D. J., Smith K. M., Fajer J., Holten D., J. Am. Chem. Soc., 1994, 116, 7363—7368

[19] Zheng W. Q., Shan N., Yu L. X., Wang X. Q., Dyes and Pigments, 2008, 77(1), 153—157

[20] Ke B. B., Wan L. S., Huang X. J., Xu Z. K., Chem. Res. Chinese Universities, 2011, 27(4), 592—594

[21] Guo X. M., Shi T. S., J. Mol. Struct., 2006, 789(3), 8—17

[22] Kadish K. M., Smith K. M., Guilard R., The Porphyrin Handbook, Academic Press, New York, 2003

[23] Chen D. M., Zhang Y. H., He T. J., Liu F. C., Spectrochimica Acta Part A, 2002, 58, 2291—2297