title: [18]/[20]π hemiporphyrazine: a redox-switchable near-infrared dye.
abstract: 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.
authors.affiliation: Advanced Elements Chemistry Research Team, RIKEN-ASI, Wako-shi, Saitama 351-0198, Japan. atsuya-muranaka@riken.jp
authors.forename: Atsuya
authors.initials: A
authors.lastname: Muranaka
authors.forename: Shino
authors.initials: S
authors.lastname: Ohira
authors.forename: Daisuke
authors.initials: D
authors.lastname: Hashizume
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Koshino
authors.forename: Fumiko
authors.initials: F
authors.lastname: Kyotani
authors.forename: Machiko
authors.initials: M
authors.lastname: Hirayama
authors.forename: Masanobu
authors.initials: M
authors.lastname: Uchiyama
mesh_terms: D004396:Coloring Agents / Q000737:chemistry*; D007259:Infrared Rays; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011166:Porphyrins / Q000737:chemistry*; D011789:Quantum Theory
chemical_list: D004396:Coloring Agents; D011166:Porphyrins