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.
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. https://doi.org/10.1002/chem.200401348
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. https://doi.org/10.1016/j.tet.2009.06.037
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.
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. https://doi.org/10.1021/ja310596a
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. https://doi.org/10.1039/C5DT01141H