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An aromatic hemiporphyrazine with an 18π-electron structure has been synthesized by oxidizing 20π-electron 8,10,21,23-tetrahydroxy-28,30-dicarba-27H,29H-hemiporphyrazine with bulky aryl ether substituents. The aromatic nature of the oxidized form was characterized by means of various spectroscopic methods and single-crystal X-ray analysis, with the help of quantum-chemical calculations. The oxidized hemiporphyrazine exhibited an intense absorption at ~850 nm. The redox process was found to be reversible.
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Muranaka et al. (2011) studied this question.
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