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Issue 22, 2019
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Synthesis of aminyl biradicals by base-induced Csp3–Csp3 coupling of cationic azo dyes

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Abstract

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.

Graphical abstract: Synthesis of aminyl biradicals by base-induced Csp3–Csp3 coupling of cationic azo dyes

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Publication details

The article was received on 27 Mar 2019, accepted on 01 May 2019 and first published on 09 May 2019


Article type: Edge Article
DOI: 10.1039/C9SC01502G
Chem. Sci., 2019,10, 5719-5724
  • Open access: Creative Commons BY-NC license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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

    Y. Liu, P. Varava, A. Fabrizio, L. Y. M. Eymann, A. G. Tskhovrebov, O. M. Planes, E. Solari, F. Fadaei-Tirani, R. Scopelliti, A. Sienkiewicz, C. Corminboeuf and K. Severin, Chem. Sci., 2019, 10, 5719
    DOI: 10.1039/C9SC01502G

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