Preparation, structure, and amphoteric redox properties of p-phenylenediamine-type dyes fused with a chalcogenadiazole unit.
4,7-Bis(dialkylamino)benzo[c][1,2,5]chalcogenadiazoles are a novel class of organic dyes that undergo reversible two-stage one-electron oxidation as well as one-electron reduction. They exhibit absorption maxima in the long-wavelength region, which are assigned as intramolecular charge transfer bands from the phenylenediamine moiety to the electron-accepting heterocycle. Their redox properties as well as molecular and crystal structures are affected by the alkyl substituents on the amino nitrogen and/or by the chalcogen atom (O, S, Se) in the heterocycle.
Suzuki
T
T
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan. tak@sci.hokudai.ac.jp
Tsuji
T
T
Okubo
T
T
Okada
A
A
Obana
Y
Y
Fukushima
T
T
Miyashi
T
T
Yamashita
Y
Y