Synthesis of a Metal-Free Texaphyrin

Authors

Sharon Hannah
Vincent M. Lynch
Nikolay GerasimchukFollow
Darren Magda
Jonathan L. Sessler

Abstract

The synthesis of a metal-free form of texaphyrin, an aromatic porphyrin-like macrocycle, is described. Previously, texaphyrins could only be obtained reproducibly in the form of metal complexes. Using ferrocenium cation as the oxidizing agent and starting with a reduced porphyrinogen-like nonaromatic form of texaphyrin, we isolated, in good yield, the metal-free oxidized texaphyrin as its HPF6 salt. This product was characterized by X-ray diffraction analysis, UV−vis spectroscopy, and cyclic voltammetry.

Document Type

Article

DOI

https://doi.org/10.1021/ol016757s

Keywords

redox reactions, metals, pyrroles, aromatic compounds, macrocycles

Publication Date

2001

Recommended Citation

Hannah, Sharon, Vincent M. Lynch, Nikolay Gerasimchuk, Darren Magda, and Jonathan L. Sessler. "Synthesis of a metal-free texaphyrin." Organic letters 3, no. 24 (2001): 3911-3914.

Journal Title

Organic letters