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

Author:

Tidwell Cynthia P.1,Bharara Prakash1,Belmore Kenneth A.2,Liang Qiaoli2,Dye Gregory W.1,Jarrett Kevin1,McKinney William1,Su Ting Yu1,Tidwell Trever1

Affiliation:

1. 1University of Montevallo, Department of Biology, Chemistry and Mathematics, UM Station 6480, Montevallo, AL 35115, USA

2. 2University of Alabama, Department of Chemistry, Box 870336, Tuscaloosa, AL 35487, USA

Abstract

AbstractPorphyrins 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.

Publisher

Walter de Gruyter GmbH

Subject

Organic Chemistry

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