Elusive in its free-base form, the core-modified contracted porphyrin thiatriphyrin(2.1.1) was prepared with p-tolyl substituents by intramolecular McMurry coupling and then converted into various alkoxy-substituted analogues (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene). In the presence of trifluoroacetic acid (TFA), each of these compounds was transformed into the protonated thiatriphyrin(2.1.1), which exhibited moderate aromaticity.
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