Reversible Redox System of 2-Oxypyritriphyrin(1.2.1) Accompanying Interconversion between 3-Pyridone and 3-Hydroxypyridine Units.

To develop a system in which a π-conjugation circuit switched by a redox reaction between 3-pyridone and 3-hydroxypyridine, a ring-contracted analog of oxypyriporphyrin, 2-oxypyritriphyrin(1.2.1) was synthesized for the first time. 2-Oxypyritriphyrin(1.2.1) contains a 14π aromatic conjugation circuit with the keto-form of the 3-oxypyridine ring. When 2-oxypyritriphyrin was treated with NaBH4 , not only the 3-oxypyridine group, but also the meso-carbons were also reduced to give a colorless porphyrinogen analog. The reduced compound could be oxidized again to provide 2-oxypyritripyhrin in a reversible manner.