Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations

Organic & Biomolecular Chemistry Pub Date: 2004-11-05 DOI: 10.1039/B412688B

Abstract

The boron trifluoride-catalyzed Rothemund condensations of phenylpropargylaldehyde with 4,7-dihydro-4,7-ethano-2H-isoindole or 3,4-diethylpyrrole in dichloromethane at low temperature give 5,10,15,20-tetrakis(phenylethynyl)porphyrins bearing bicyclo[2.2.2]octadiene and octaethyl substituents, respectively. The former undergoes a retro Diels–Alder reaction to afford 5,10,15,20-tetrakis(phenylethynyl)benzoporphyrin quantitatively. The different conformations of the porphyrin periphery were determined by X-ray diffraction and their redox and spectroscopic properties have been investigated.

Graphical abstract: Controlling conformations and physical properties of meso-tetrakis(phenylethynyl)porphyrins by ring fusion: synthesis, properties and structural characterizations
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