Meso-Formyl, Vinyl, and Ethynyl Porphyrins-Multipotent Synthons for Obtaining a Diverse Array of Functional Derivatives

Molecules. 2023 Jul 31;28(15):5782. doi: 10.3390/molecules28155782.

Abstract

This review presents a strategy for obtaining various functional derivatives of tetrapyrrole compounds based on transformations of unsaturated carbon-oxygen and carbon-carbon bonds of the substituents at the meso position (meso-formyl, vinyl, and ethynyl porphyrins). First, synthetic approaches to the preparation of these precursors are described. Then diverse pathways for the transformations of the multipotent synthons are discussed, revealing a variety of products of such reactions. The structures, electronic, and optical properties of the compounds obtained by the methods under consideration are analyzed. In addition, there is an overview of the applications of the products obtained. Biomedical use of the compounds is among the most important. Finally, the advantages of using the reviewed synthetic strategy to obtain dyes with targeted properties are highlighted.

Keywords: Glaiser coupling; Heck reaction; Sonogashira reaction; Vilsmeier–Haack formylation; meso-ethynylporphyrin; meso-formylporphyrin; meso-functionalized porphyrin; meso-vinylporphyrin; porphyrin synthon; schiff base; wittig reaction.

Publication types

  • Review