Synthesis and Characterization of Meso-Tetra (o-nitro) phenyltetraphenylporphyrin (Ⅳ)

Hengliang Zhang, Hongxia Liao, Minqin Li


Benzoporphyrin is a porphyrin derivative with β-pyrrole ring and benzene ring. It is a macrocyclic aromatic compound with 18π electron structure. Because of the benzene ring, the porphyrin conjugation system is expanded, which enriches the π-electrons with special structure and properties. Therefore, it has a wide range of applications and can be used as a new type of photosensitizing molecules. It shows good application in light functional materials prospect. In this paper, the thermo-coagulation method was used to synthesize the intermediate-tetrakis (o-nitro) n phenyltetraphenylpyridinium zinc (Ⅱ) (P-phenanthroline) by using potassium phthalimide, o-nitrophenylacetic acid and zinc acetate as raw materials. With hydrochloric acid and glacial acetic acid zinc ions were removed in the ice water bath, resulting in the media-tetra (o-nitro) phenyl tetraphenylporphyrin. Under microwave heating, the median-four (O-nitro) phenyl tetraphenylporphyrin (Ⅳ) was prepared by the reaction of o-nitro-phenyl-tetraphenylporphyrin with stannous chloride. These compounds were characterized using UV and infrared spectroscopy.

Full Text:



Zhang Hongfen, Pan Jinghao. Porphyrin and metalloporphyrin [J]. Chemistry Education, 2005,26 (4): 78-80.

ZHAO Sheng-fang, YANG Shui-bin, ZHENG Yan Preparation and application of substituted tetraphenylporphyrin compounds [J]. Journal of Huanggang Normal University, 2004,21 (3): 56-58.

Kalyanasundaram K, Neumann S M. Photophysical and redox properties of water-soluble porphyrins in aqueous media [J]. Synthetic Comm, 1982, 13 (26): 23-27.

Zhang Hongxia, Li Qingshan, Ren Jianguo. Synthesis and spectral properties of tetraphenylporphyrin derivatives and their metal complexes [J]. Journal of Shanxi Medical University, 2000,31 (6): 47-49.

Chen Danyou, Zhao Shengfang. Study on UV - Vis spectra of Three Substituted Tetraphenylporphyrin Compounds [J]. Journal of Huanggang Normal University, 2003,6 (3): 34-36.

Synthesis and Spectroscopic Properties of β-Nitro-tetraphenylporphyrin and Zinc [J]. Chemical Reagents, 2002,24 (5): 268 ~ 270.

Li Fangliang, Nong Lanping. New application of microwave technology in chemistry [J]. Guangxi Science, 2004,8 (2): 13-15.

Hu Minxue, Wang Daiyuan. Synthesis and Spectroscopic Properties of Meso - Phenyltetraphenylporphyrin [J]. Photographic Science and Photochemistry, 1996,14 (3): 34-37.

Liu Hongtao, Zhou Danhua, Zhou Guiju. Synthesis of tetraphenylporphyrin by microwave irradiation [J]. Chemical Technology and Development, 2009,17 (4): 16-18.

HAO Xiao-ling, HAN Shi-tian, LIU Yan-qin. Advances in chemical studies of porphyrin and metalloporphyrin complexes [J]. Journal of Hebei Normal University (Natural Science Edition), 2009,23 (6): 67-70.

LIU Xin-gang, FENG Ya-qing.Progress in the Application and Synthesis of Porphyrin Compounds [J]. Chemical Propellants and Polymeric Materials. 2004,

Duan Zhenning, Shen Yilong, Fu Xiang. Synthesis and application of porphyrin and metalloporphyrin compounds [J]. Journal of Beijing Institute of Light Industry, 1995,25 (2): 70-74.

Chen Danyou, Zhao Shengfang, Liao Xuehong. Microwave synthesis of tetraphenylporphyrin [J]. Journal of Wuhan University (Science Edition), 2004,50 (2): 169-172.

Kazunori S, Masayuki T. Conducting polymer networks cross-linked byisolatedfunctional dyes: design, synthesis, and electrochemical polymerization of doubly strapped light-harvesting porphyrin / oligothiophene monomer [J]. Chem Eur J, 2009, 25 (15): 6350 -6362.

Dong Runan, Qiu Yong, Song Xinqi. Photocatalytic oxidation of porphyrin compounds to biomolecules [J]. Progress in Chemistry, 1998,10 (1): 45-54.

M Biesaga, K Pyrzynska., M Trojanowicz. Porphyrins in analytical chemistry [J]. Areview Talanta, 2000, 51 (2): 209-224.

Yu Kegui, Zhou Chenghe, Li Donghong. New progress in porphyrin anticancer drugs [J]. Journal of Chemical Research and Application, 2007,8 (12): 19-12.

Synthesis of porphyrin compounds [J]. Chemical Progress, 2007,19 (4): 520-526.

YANG Shui-bin, LIAO Xue-hong Synthesis and characterization of tin (IV) in meso-tetra (o-nitrophenyl) tetraphenylporphyrin [J] 1998 11.

HANG Yu-xia, HAN Shi-tian, LIU Yan-qin.Progress and research progress of porphyrin and its derivatives [J]. Chemical Engineering and Equipment, No.6, 2008.

ZHU Zhen-ping, REN Jianguo, QIN Zibin. Electrochemical properties of meso-tetrakis (o-nitro) phenyltetraphenylporphyrin and its transition metal complexes [J]. Chinese Journal of Chemical Research and Application, Vol. 6 3 period.



  • There are currently no refbacks.

Creative Commons License

This site is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.