Porphyrins and related systems have been widely investigated and show promising properties for applications, including as photosensitizers for photodynamic therapy. For applications of this type, the presence of long wavelength absorptions is beneficial. Recently, a carbaporphyrin structure with a fused tropolone unit was shown to have highly modified spectroscopic properties. In order to further investigate this phenomenon, porphyrin and heteroporphyrin structures with fused tropone rings have been targeted for synthesis. Base-catalyzed condensation of diethyl acetonedicarboxylate with 2,5-dimethylpyrrole-3,4-dicarbaldehyde gave a tropone-fused pyrrole 1a and subsequent reaction with lead tetraacetate afforded a diacetate derivative 1b. Further condensation with an a-unsubstituted pyrrole then gave a tripyrrane intermediate 2. Ongoing studies are being directed towards the preparation of modified porphyrin chromophores from this key intermediate.

Synthesis of tropone-fused porphyrins

255th National Meeting (2018)

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