All Title Author
Keywords Abstract

Preparation of Single Substituted Phenyl Porphyrins Form Meso-Tetraphenyl Porphyrin-Synthetic Example from Symmetric Porphyrin into Asymmetric Porphyrins

DOI: 10.4236/ojic.2018.81002, PP. 21-27

Keywords: Asymmetric Porphyrin, Spectral Characterization, Redox, Chloromethylation, Formylation

Full-Text   Cite this paper   Add to My Lib


Two asymmetric porphyrins, 5-(4-chloromethylphenyl)-10, 15, 20-triphenyl porphyrin and 5-(4-formylphenyl)-10, 15, 20-triphenyl porphyrin, were successfully prepared by the symmetric meso-tetraphenyl porphyrin and relative molecular configurations and properties were characterized by spectral determinations. This work presented an example for synthesis of asymmetric porphyrin derivatives from the symmetric porphyrin. Both asymmetric porphyrins are reactive in molecular assembly, the concerned reactions including alkylation with Grignard reagents, etherification with alcohols, aldol condensation and Mannich reaction for modification and enhancing their functionality. In this work, the reaction conditions were improved, synthetic strategy and route were confirmed.


[1]  Maier, S., Fendt, L.-A., Zimmerli, L., Glatzel, T., Pfeiffer, O., Diederich, F. and Meyer, E. (2008) Nanoscale Engineering of Molecular Porphyrin Wires on Insulating Surfaces. Small, 4, 1115-1118.
[2]  Vail, S.A., Krawczuk, P.J., Guldi, D.M., Palkar, A., Echegoyen, L., Tom, J.P.C., Fazio, M.A. and Schuster, D.I. (2005) Energy and Electron Transfer in Polyacetylene-Linked Zinc-Porphyrin-Fullerene Molecular Wires. Chemistry—A European Journal, 11, 3375-3388.
[3]  Bakar, M.B., Oelgemller, M. and Senge, M.O. (2009) Lead Structures for Applications in Photodynamic Therapy. Part 2: Synthetic Studies for Photo-Triggered Release Systems of Bioconjugate Porphyrin Photosensitizers. Tetrahedron, 65, 7064-7078.
[4]  Liang, X., Li, X., Yue, X. and Dai, Z. (2011) Conjugation of Porphyrin to Nanohybrid Cerasomes for Photodynamic Diagnosis and Therapy of Cancer. Angewandte Chemie International Edition, 50, 11622-11627.
[5]  Son, H.-J., Jin, S., Patwardhan, S., Wezenberg, S.J., Jeong, N.C., So, M., Wilmer C.E., Sarjeant, A.A., Schatz, G.C., Snurr, R.Q., Farha, O.K., Wiederrecht, G.P. and Hupp, J.T. (2013) Light-Harvesting and Ultrafast Energy Migration in Porphyrin-Based Metal-Organic Frameworks. Journal of the American Chemical Society, 135, 862-869.
[6]  Zervaki, G.E., Tsaka, V., Vatikioti, A., Georgakaki, I., Nikolaou, V., Sharma, G.D. and Coutsolelos, A.G. (2015) A Triazine Di(Carboxy)Porphyrin Dyad versus a Triazine Di(Carboxy)Porphyrin Triad for Sensitizers in DSSCs. Dalton Transactions, 44, 13550-13564.
[7]  Jia, X.L. (2006) Synthesis and Property Research of Novel Porphyrin. Master Thesis, Zhejiang University, Hangzhou, 43-47.
[8]  Lindsey, J.S., Schreiman, I.C., Hsu, H.C., Kearney, P.C. and Marguerettaz, A.M. (1987) Rothemund and Adler-Longo Reactions Revisited: Synthesis of Tetraphenylporphyrins under Equilibrium Conditions. The Journal of Organic Chemistry, 52, 827-836.


comments powered by Disqus