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A recent study on magnetically induced currents in 10-isocorrole derivatives indicated that both the free-base and metal-complexed forms of the unsubstituted macrocycle are homoaromatic. Furthermore, depending on the substituents at the 10-position, the aromatic character was found to swing between substantially homoaromatic to substantially antihomoaromatic. Heteroisocorroles, in which the saturated 10-position has been replaced by a heteroatom-containing group X, are predicted to exhibit even more dramatic variations in aromatic character, ranging from strongly aromatic (X = O, NH, PH, and S) to strongly antiaromatic (X = BH and CO). Interestingly, the experimentally studied X = SiMe 2 case does not appear to sustain a significant global ring current.

Magnetic Diversity in Heteroisocorroles: Aromatic Pathways in 10-Heteroatom-Substituted Isocorroles