Synthesis and spectral evaluation of 5,10,15,20-tetrakis(3,4-dibenzyloxyphenyl)porphyrin

Abstract

Porphyrins are of interest in many applications that involve electron transfer and absorption of light, such as solar energy and photodynamic cancer therapy. The newly synthesized 5,10,15,20-tetrakis(3,4-dibenzyloxyphenyl)porphyrin, TDBOPP, was characterized using 1H NMR, 13C NMR, UV-vis and fluorescence spectroscopy and MALDI-TOF/TOF high resolution mass spectrometry. Standard 1H NMR and 13C NMR experiments coupled with nuclear Overhauser effect (NOE) experiments confirmed the structure of the compound. The expected M+ and [M+H]+ ions are observed in the MALDI-TOF/TOF mass spectrum. The UV-vis absorption spectrum of TDBOPP shows a Soret band at 424 nm and three Q bands at 519 nm, 556 nm, and 650 nm with molar absorptivity 3.6×105 cm−1m−1, 1.6×104 cm−1m−1, 1.0×104 cm−1m−1 and 5.3×103 cm−1m−1, respectively. Excitation at 424 nm gives emission at 650 nm. The quantum yield of the porphyrin is 0.11.

Copper 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin

“…Copper 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin (TDBOPP) was synthesized as previously reported [10]. Copper 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin was prepared using TDBOPP (0.1580 g, 1.079 × 10 −4 mol) in 50.0 mL of boiling chloroform.…”