Synthesis and electrochemical characterization of dipyrroles separated by diphenyleneoxide and diphenylenesulfide spacers via the Trofimov reaction

• Published in: Tetrahedron 2005-08, Vol.61 (32), p.7756-7762
• Main Authors: Vasil'tsov, Alexander M., Schmidt, Elena Yu, Mikhaleva, Al'bina I., Zorina, Nadezhda V., Zaitsev, Alexey B., Petrova, Olga V., Krivdin, Leonid B., Petrushenko, Konstantin B., Ushakov, Igor' A., Pozo-Gonzalo, Cristina, Pomposo, José A., Grande, Hans-Jürgen
• Format: Article
• Language: English
• Subjects: Acetylene; Dioximes; Diphenyleneoxide spacer; Diphenylenesulfide spacer; Dipyrroles; Electropolymerization; Luminescence; Superbase
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2005.05.088

4,4′-Bis[2-(1-vinylpyrrolyl)]diphenyloxide, 4,4′-bis(2-pyrrolyl)diphenylsulfide, 4-(2-pyrrolyl)-4′-[2-(1-vinylpyrrolyl)]diphenylsulfide and 4,4′-bis[2-(1-vinylpyrrolyl)]diphenylsulfide have been synthesized in a one-pot procedure from oximes of corresponding diacetylphenylenoxide and -sulfide through their reaction with acetylene in the MOH–DMSO systems (M=Li, K) at 80–130 °C under pressure of 10–15 atm, thus illustrating applicability and general character of the reaction of synthesis of diverse dipyrrole–phenylene assemblies and their N-vinyl derivatives. Two of the pipyrroles are promising for creating new conducting polymers with sulfur and oxygen atoms in the conjugation chain and for the study of the influence of the diphenyleneheteroatom moiety on conductivity of final polymer products. For the dipyrroles with the diphenyleneheteroatom moieties and 1,4-phenylene spacer the luminescence characteristics were determined. Graphical Abstract