title: A peroxide-bridged imidazole dimer formed from a photochromic naphthalene-bridged imidazole dimer.
abstract: 2,4,5-Triphenylimidazole (lophine) is known as the first chemiluminescence substrate, and its oxidized derivative, the 2,4,5-triphenylimidazolyl radical, corresponds to the coloured species in the photochromic reaction of hexaarylbiimidazole (HABI). We report the first direct observation of the O(2) adduct of the imidazolyl radical that forms the end-on peroxide-bridged imidazole dimer. The ring-opening reaction of the peroxide-bridged imidazole dimer leading to the formation of an N-benzoylbenzamidine derivative supports the presence of the 4,5-epidioxide of lophine as a reaction intermediate of its chemiluminescence.
authors.affiliation: Department of Chemistry, School of Science and Engineering, Aoyama Gakuin University, 5-10-1 Fuchinobe, Sagamihara, Kanagawa 252-5258, Japan.
authors.forename: Sayaka
authors.initials: S
authors.lastname: Hatano
authors.forename: Jiro
authors.initials: J
authors.lastname: Abe
mesh_terms: D018360:Crystallography, X-Ray; D019281:Dimerization; D007093:Imidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D009281:Naphthalenes / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry; D010545:Peroxides / Q000737:chemistry*; D055668:Photochemical Processes
chemical_list: D007093:Imidazoles; D009281:Naphthalenes; D010545:Peroxides; C031721:naphthalene; D010100:Oxygen