Synthesis and characterization of novel porphyrin-cinnamic acid conjugates

A series of novel porphyrin-cinnamic acid (porphyrin/CA) conjugates (4a-4c) have been synthesized by condensation of 5-(4-Hydroxyphenyl)-10,15,20-triphenyl- porphyrin (1) with different substituted cinnamic acids (CAs) through an alkyl linker due to the biological activities of CAs and the application of porphyrins in photodynamic therapy (PDT) of cancer. Their related zinc (II) complexes (5a-5c) were also prepared. These novel compounds have been fully characterized by ¹H NMR, Infrared (IR), Mass spectra (Ms) and Elemental analysis. The photophysical properties of these target molecules were studied by absorption and Fluorescence spectroscopy. In solution, the effect of pH, ionic strength in acid media and concentration on the aggregation behaviors of 4a has also been investigated by UV-Vis spectra. The broadened and red shifted Soret band indicated the formation of J-aggregates when the pH value was up to 2.0 in THF-aqueous solution. Furthermore, the higher ionic strength of 0.3 M NaCl in acid media resulted in the generation of J-aggregates in THF-aqueous solution. And the significant blue shift of Soret band also demonstrated the formation of H-aggregates of 4a at 1.1 × 10^-4 M in THF.