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4,7-Bis(dimethylamino)benzimidazoles and twin-type derivatives: reversible two-stage redox system modulated by proton-transfer
Authors:Takanori Suzuki  Yoshiaki TsubataYoshiaki Obana  Takanori FukushimaTsutomu Miyashi  Mayu SaitoHidetoshi Kawai  Kenshu FujiwaraKimio Akiyama
Institution:a Division of Chemistry, Graduate School of Science, Hokkaido Universiy, Sapporo 060-0810, Japan
b Department of Chemistry, Graduate School of Science, Tohoku Universiy, Sendai 980-8578, Japan
c Institute of Multidisciplinary Research for Advanced Materials, Tohoku University, Sendai 980-8577, Japan
Abstract:The title electron donors 1 as well as their conjugate bases 2 undergo reversible two-stage one-electron oxidation. ESR analysis indicated the important contribution of zwitterionic structure for radicals 2radical dot. Bis(zwitterionic) but not quinoid structure was suggested for p-4, generated from the twin-type dianionic donor p-42− with a p-phenylene spacer.
Keywords:electron donor  proton transfer  phenylenediamine  radical  zwitterion  redox system  electrochromism  response system
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