Synthesis and characterization of 5,10,15,20-tetra[4-(2,3-epoxypropoxy)phenyl]porphyrin

doi:10.3969/j.issn.1000-1565.2015.01.009

Abstract

Abstract: 5,10,15,20-tetra(4-hydroxylphenyl)porphyrin (THPP) was synthesized by using p-hydroxybenzaldehyde and pyrrole as raw materials, propionic acid, acetic acid and nitrobenzene as solvent. 5,10,15,20-tetra[4-(2,3-epoxypropoxy)phenyl]porphyrin (TEPPP) was prepared by using THPP and epichlorohydrin as materials in isopropanol with sodium hydroxide as catalyst. The chemical structure and optical properties of THPP and TEPPP were characterized and tested by Fourier transform infrared spectrometer (FTIR), nuclear magnetic resonance spectrometer (NMR), ultraviolet-visible (UV-Vis) spectrophotometer and spectrofluorophotometer, respectively. The absorption peaks at 1 349 cm-1 and 916 cm-1 are attributed to C = N bond stretching vibration absorption peaks of TEPPP porphyrin ring and C―O―C bond asymmetric stretching vibration absorption peak of epoxide ring in FTIR spectrum of TEPPP, respectively. In 1H NMR spectrum of TEPPP, the peak area ratio of 5 chemical shift peaks was 1:1:1:1:1 between 2.92 ppm to 4.60 ppm, which was consisted with the ratio of the hydrogen atom number of epoxy group. The absorption peaks of TEPPP were similar to those of porphyrin in UV-Vis spectrum. The fluorescence properties of THPP and TEPPP were studied by fluorescence spectroscopy and fluorescence quantum yield were 0.08 and 0.16, respectively.

Key words: porphryrin, 5,10,15,20-tetra[4-(2,3-epoxypropoxy)phenyl]porphyrin, ultraviolet-visible spectroscopy, fluorescence spectroscopy, fluorescence quantum yield

CLC Number:

O631.5

WANG Miaomiao, LIU Yaojun, WANG Yuan, WANG Yaohui, ZHAO Hongchi. Synthesis and characterization of 5,10,15,20-tetra[4-(2,3-epoxypropoxy)phenyl]porphyrin[J]. Journal of Hebei University (Natural Science Edition), 2015, 35(1): 48-53.

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