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

被引：19

作者：

Calvete, Mario J. F. ^{[1
]}

Dias, Lucas D. ^{[1
]}

Henriques, Cesar A. ^{[1
]}

Pinto, Sara M. A. ^{[1
]}

Carrilho, Rui M. B. ^{[1
]}

Pereira, Mariette M. ^{[1
]}

机构：

[1] Univ Coimbra, Coimbra Chem Ctr, Fac Ciencias & Tecnol, CQC,Dept Quim, Rua Larga, P-3004535 Coimbra, Portugal

来源：

MOLECULES | 2017年 / 22卷 / 05期

关键词：

unsymmetrical porphyrins; inorganic acid catalysis; alternative synthetic methodologies; TETRAPYRROLIC MACROCYCLES; DERIVATIVES; PHTHALOCYANINES; SUBSTITUENTS; OXIDATION; QUEST; TOOL; NMR;

D O I：

10.3390/molecules22050741

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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.

引用

页数：11

共 65 条

[11] 19F NMR: a valuable tool for studying biological events [J].