Quinonoidal subporphyrin analogue 2 was synthesized by oxidation of meso-tris(3,5-di-tert-butyl-4-hydroxyphenyl)subporphyrin 1 (see scheme). Compound 2 was readily deprotonated to generate anionic species 3. These three macrocycles were structurally characterized, including the full delocalization of the anionic charge in 3.
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Hayashi et al. (2011) studied this question.
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