Synthesis, characterization and Twin Polymerization of a novel dioxagermine

•Full characterization including MS, XRD and DFT-D of a novel benzo[d]dioxagermine.•Twin Polymerization of germanium compounds.•Organic–inorganic hybrid materials starting from a germanium precursor.•Ortho quinone methide as reactive intermediate in Twin Polymerization.

The synthesis of 6-bromo-2,2-di-tert-butyl-4H-1,3,2-benzo[d]dioxagermine (1) via an alcohol/alkoxide exchange starting from di-tert-butyl-di-ethoxy germane is reported. Characterization of the title compound including single crystal X-ray diffraction and TGA/DSC analysis, mass spectrometry, 1H NMR, 13C{1H} NMR and IR spectroscopy is reported. DFT-D calculations have been carried out to assign the absorption band maxima of the IR spectrum to the corresponding vibrational modes. The suitability for Twin Polymerization of the novel dioxagermine 1 has been studied by TGA/DSC analysis and mass spectrometry. Proton-assisted Twin Polymerization of 1 results in an organic–inorganic hybrid material composed of a phenolic resin and [tBu2GeO]n.

Graphical abstractThe synthesis and full characterization including XRD and DFT-D analysis of a novel dioxagermine, 6-bromo-2,2-di-tert-butyl-4H-1,3,2-benzo[d]dioxagermine, is presented. Its suitability for Twin Polymerization has been studied by TGA/DSC analysis and mass spectrometry. Proton-assisted Twin Polymerization results in an organic–inorganic hybrid material composed of a phenolic resin and [tBu2GeO]n.Figure optionsDownload full-size imageDownload as PowerPoint slide