Journal of the American Chemical Society, Vol.134, No.1, 190-193, 2012
[18]/[20]pi Hemiporphyrazine: A Redox-Switchable Near-Infrared Dye
An aromatic hemiporphyrazine with an 18 pi-electron structure has been synthesized by oxidizing 20 pi-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 similar to 850 nm. The redox process was found to be reversible.