Meso-tetra(dioxanyl)porphyrins: Neutral, low molecular weight, and chiral porphyrins with solubility in aqueous solutions

Author:

Jiang Xu-Liang12,Damunupola Dinusha1,Bruckner Christian1

Affiliation:

1. Department of Chemistry, University of Connecticut, 55 N Eagleville Rd., Storrs, CT 06269-3060, USA

2. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China

Abstract

The synthesis of the low-molecular weight, meso-tetra(dioxan-2-yl)porphyrin with considerable solubility in aqueous solution is described. The key intermediate dioxan-2-carbaldehyde is accessible in either racemic or in stereo-pure forms from commercially available starting materials in three steps. Using 4 × 1 or 2 + 2-type syntheses provide the porphyrin in modest yields. While the racemic aldehyde created an intractable mixture of diastereomers, the enantiopure aldehyde created a single enantiomer of the target porphyrin. The porphyrin was spectroscopically characterized. As its free base or zinc complex, it showed excellent solubility properties in organic and aqueous solvents, though free water-solubility was not achieved. The work expands on the availability of chiral porphyrins and neutral porphyrins with considerable solubility in aqueous solution.

Publisher

World Scientific Pub Co Pte Lt

Subject

General Chemistry

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