Unexpected metal-mediated oxidation of hydroxymethyl groups to coordinated carboxylate groups by bis-cyclometalated iridium(III) centers

Beatrice Beyer; Christoph Ulbricht; Andreas Winter; Martin D. Hager; Richard Hoogenboom; Nicole Herzer; Stefan O. Baumann; Guido Kickelbick; Helmar Görls; Ulrich S. Schubert

doi:10.1039/B9NJ00785G

Unexpected metal-mediated oxidation of hydroxymethyl groups to coordinated carboxylategroups by bis-cyclometalated iridium(iii) centers†

Beatrice Beyer,^a Christoph Ulbricht,^bc Andreas Winter,^bc Martin D. Hager,^ac Richard Hoogenboom,^b Nicole Herzer,^b Stefan O. Baumann,^d Guido Kickelbick,^de Helmar Görls^f and Ulrich S. Schubert*^abc

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^a Laboratory of Organic and Macromolecular Chemistry, Friedrich-Schiller-University Jena, Humboldtstr. 10, 07743 Jena, Germany
E-mail: ulrich.schubert@uni-jena.de
Fax: +49 3641 948202
Tel: +49 3641 948200

^b Laboratory of Macromolecular Chemistry and Nanoscience, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven, The Netherlands

^c Dutch Polymer Institute (DPI), P.O. Box 902, 5600 AZ Eindhoven, The Netherlands

^d Institute of Materials Chemistry, Vienna University of Technology, Getreidemarkt 9/165, 1060 Vienna, Austria

^e Inorganic Solid State Chemistry, Saarland University, Am Markt Zeile 3, 66125 Saarbrücken, Germany

^f Laboratory of Inorganic and Analytic Chemistry, Friedrich-Schiller-University Jena, Lessingstr. 8, 07743 Jena, Germany

Abstract

Two different procedures of the ‘click’ reaction were applied to synthesize a library of 1-aryl- and 4-aryl-functionalized 1H-[1,2,3]triazoles as new ligands for phosphorescent iridium(III) complexes. For three examples, single crystal X-ray analysis was carried out and the structural properties were discussed. The reactive μ-dihydroxy-bridged iridium(III) precursor complex [(ppy)₂Ir-μ-(OH)]₂ (ppy = 2-phenylpyridinato) was prepared for the complexation of the herein described ligands. During these complexation studies, an unexpected metal-assisted oxidation pathway was observed for the hydroxymethyl-substituted 1-aryl-1H-[1,2,3]triazoles 2d–f leading selectively to a [carboxylate-N³,O]-coordination of the ligands to the iridium(III) centers.

New Journal of Chemistry

Unexpected metal-mediated oxidation of hydroxymethyl groups to coordinated carboxylategroups by bis-cyclometalated iridium(iii) centers†

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Unexpected metal-mediated oxidation of hydroxymethyl groups to coordinated carboxylate groups by bis-cyclometalated iridium(III) centers

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