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. A carbaporphyrin structure with a fused tropone unit has previously been shown to have highly modified spectroscopic properties. In order to further investigate this phenomenon, the synthesis of porphyrins and porphyrin analogues with similarly fused tropone rings were targeted. A tropone-fused tripyrrane 1 was prepared in three steps from pyrrole 2. The tert-butyl ester groups were cleaved with trifluoroacetic acid and the deprotected tripyrrane was condensed with a series of dialdehydes to give tropone-fused porphyrinoids 3-8. All of these macrocycles retained strongly aromatic properties but the UV-vis spectra were highly modified and bathochromically shifted. Syntheses of related systems are currently in progress.

Modification of porphyrinoid chromophores by the introduction of fused tropone units

2019 Spring National Meeting

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