Porphyrins, known as “organic dyes," are aromatic macrocycles which possess a variety of interesting properties. Porphyrins have broad applications ranging from biomedicines to organic electronics. The specific properties of porphyrins can be adjusted and fine-tuned through the addition of different substituents to the porphyrin ring. Pi-extension of the porphyrin ring can significantly impact the photochemical and electrical properties of porphyrins. Therefore, it is of interest to develop novel synthetic pathways to further the range of possible pi-extended substituents to the porphyrin core structure.<br/>In this project, di-brominated and tetra-brominated porphyrins were prepared for further development of new syntheses of pi-extended porphyrins and for investigations into their properties. The di-brominated and tetra-brominated porphyrins were obtained in good yields. The di-brominated and tetra-brominated porphyrins display much red-shifted and broadened absorption bands as compared to their parent porphyrins. The emission bands of these brominated porphyrins show similar trends. A monobenzoporphyrin carrying aldehyde substituents was prepared from these bromoporphyrins through a Heck-based cascade reaction, confirming the expected changes in absorption bands from the base porphyrin.

Building the basis for novel syntheses of pi-extended porphyrins

2019 Spring National Meeting

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