Towards hydrocarbon analogues of the porphyrins: synthesis and spectroscopic characterization of the first dicarbaporphyrin†

Abstract

Condensation of 3,4-diethylpyrrole with 1,3-diformylindane in the presence of catalytic HBr afforded, following oxidation with FeCl₃, the first example of a dicarbaporphyrin in moderate yield; this novel bridged annulene system retains a strong diamagnetic ring current in ¹H NMR spectroscopy as well as a porphyrin-like UV–VIS spectrum.

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