A Cost-Efficient Method for Unsymmetrical Meso-Aryl Porphyrin Synthesis Using NaY Zeolite as an Inorganic Acid Catalyst

• Autor(a) principal: Calvete, Mário J. F.
• Data de Publicação: 2017
• Outros Autores: Dias, Lucas D., Henriques, César A., Pinto, Sara M. A., Carrilho, Rui M. B., Pereira, Mariette M.
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• DOI: 10.3390/molecules22050741
• Texto Completo: http://hdl.handle.net/10316/108279; https://doi.org/10.3390/molecules22050741
• topic: unsymmetrical porphyrins; inorganic acid catalysis; alternative synthetic methodologies; Carbon-13 Magnetic Resonance Spectroscopy; Catalysis; Porphyrins; Proton Magnetic Resonance Spectroscopy; Sodium; Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; Yttrium; Zeolites; Cost-Benefit Analysis

Herein we report the synthesis of unsymmetrical meso-aryl substituted porphyrins, using NaY zeolite as an inorganic acid catalyst. A comparative study between this method and the several synthetic strategies available in the literature was carried out. Our method presented a better, more cost-efficient rationale and displayed a significantly lower environmental impact. Furthermore, it was possible to verify the scalability of the process as well as the reutilization of the inorganic catalyst NaY (up to 6 times) without significant yield decrease. In addition, this method was applied to the synthesis of several other unsymmetrical porphyrins, from a low melting point porphyrin to mono-carboxylated halogenated unsymmetrical porphyrins, in yields higher than those found in the literature. Additionally, for the first time, two acetamide functionalized halogenated porphyrins were prepared in high yields. This methodology opens the way to the preparation of high yielding functionalized porphyrins, which can be easily immobilized for a variety of applications, either in catalysis or in biomedicine.