Synthesis of aminyl biradicals by base-induced Csp3-Csp3 coupling of cationic azo dyes.
Journal article

Synthesis of aminyl biradicals by base-induced Csp3-Csp3 coupling of cationic azo dyes.

  • Liu Y Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Varava P Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Fabrizio A Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Eymann LYM Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Tskhovrebov AG Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Planes OM Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Solari E Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Fadaei-Tirani F Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Scopelliti R Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Sienkiewicz A Institute of Physics , EPFL , Switzerland.
  • Corminboeuf C Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
  • Severin K Institut des Sciences et Ingénierie Chimiques , Ecole Polytechnique Fédérale de Lausanne (EPFL) , 1015 Lausanne , Switzerland . Email: kay.severin@epfl.ch.
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  • 2019-07-12
Published in:
  • Chemical science. - 2019
English The synthesis of the industrially important polymer parylene is achieved by polymerization of p-quinodimethane (p-QDM). The polymerization is thought to proceed via a biradical p-QDM dimer, but isolation or characterization of such a biradical has remained elusive. Here, we describe the synthesis of an aza-analogue of this p-QDM dimer. The biradical is formed by base-induced dimerization of an azoimidazolium dye. Due to the presence of sterically shielded aminyl radicals instead of terminal H2Ċ groups, the stability of this dimer is sufficient for analyses by ESR spectroscopy and X-ray crystallography. A similar Csp3-Csp3 coupling was observed for an azotriazolium dye, suggesting that base-induced C-C coupling reactions can be realized for different types of azo dyes.
Language
  • English
Open access status
gold
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Persistent URL
https://sonar.ch/global/documents/16387
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