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A soluble and stable core-modified octaphyrin MC-T8 containing eight thiophene rings was synthesized by a new Yamamoto-coupling-followed-by-oxidative dehydrogenation protocol. X-ray crystallographic analysis revealed a nearly planar backbone, and the molecule is globally aromatic with a dominant 38π conjugation pathway. The dication MC-T8 2+ is antiaromatic and the backbone is distorted, with a different orientation of the thiophene rings. The tetracation MC-T8 4+ becomes aromatic again, with a shallow bowl-shaped geometry. Both the neutral and dication demonstrated open-shell diradical character with a small singlet-triplet energy gap (-2.70 kcal/mol of MC-T8 and -3.78 kcal/mol for MC-T8 2+ ), and they are stable due to effective spin delocalization.
This article was published in the following journal.
Name: Angewandte Chemie (International ed. in English)
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