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32π‐antiaromatic expanded isophlorins with a varying number of thiophene and furan rings adopt either planar, ring‐inverted, or twisted conformations depending on the number of furan rings in the macrocycle. However, they exhibit identical reactivity with respect to their oxidation to aromatic 30π‐dicationic species under acidic conditions. These 32π‐antiaromatic macrocycles can also be oxidized with...
Partial core‐modification of a porphyrin can be employed to synthesize the 20π antiaromatic isophlorin. Unlike the tetra‐, tri‐, and dipyrrole derivatives of a porphyrin, a monopyrrole porphyrin exhibits antiaromatic characteristics. It undergoes a two‐electron reversible ring oxidation to yield the 18π aromatic dication. 1H NMR analysis provides distinct evidence of the altered electronic characteristics...
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