Synthesis And Spectral Properties Of A Series Of Porphyrin Compounds

Porphyrin macrocycles are natural compounds and in the organism’s metabolism they play a very important role. Synthetic porphyrins and their complexes have always caused the attention of many scholars. Porphyrin applied in photodynamic therapy as a photosensitizer for killing tumor cells, and in the dye-sensitized solar cell the metal porphyrins exhibited excellent photoelectric effect. Metallloporphyrins were also widely used in catalytic reactions as high selective catalysts. Porphyrin compounds also also applied in the areas of molecular recognition and assembly of molecular devices. Based on the excellent optical, electrical and magnetic properties of porphyrin compounds, in this paper we synthesised three single-hydroxyphenyl porphyrin compounds, four alkoxyphenyl porphyrin compounds, and the product were finely characterized by spectral determinations.. We also revealed spectral changes of meso-tetra (4-nitrophenyl) porphyrin under ultraviolet irradiation in several organic solutions cuased by recognization of HC1 molecules by hydrogen bonding interactions. This thesis divided into four chapters.Chapter 1 introduced the research progress of porphyrin compounds and the research background for this thesis.Chapter 2 discussed the synthesis and characterizationof single-hydroxyphenyl porphyrins:Classical methods of synthesis of macrocyclic porphyrin molecules was adopted with different proportions of raw materials, including dubstituted benzaldehyde, pyrrole in xylene solution for, synthesisof three single-hydroxyphenyl porphyrins. Using silica gel as the stationary phase and dichloromethane as the mobile phase to purify the products by column chromatography. And the purified products were characterized by 1H NMR, UV-Vis, Fluorescence and IR spectroscopy.Chapter 3 described the synthesis and purification of meso-tetra(4-hydroxylphenyl) porphyrin(THPP) and reactions of THPP with different halogenated hydrocarbons:THPP reacting respectively with different alkyl chlorides and bromides, produced different tetra(alkoxyphenyl) porphyrin compounds, and the products were also examined by determinations of UV-Vis, IR, Fluorescence, EPR and 1H-NMR.In chapter 4 The change of UV-vis spectra were used to identify the role of the meso-tetra(4-nitrophenyl) porphyrin molecules in recognition of HC1 molecules. The influences of irradiation time, organic solvent and adding of water were invstigated in detail. Experimental results showed that with the increase of irradiation time result in enhancing spectral and redshift.