Chemistry - A European Journal
Chemistry - A European Journal
5 years ago

Arylthio- and Arylseleno-Substituted s-Heptazines

Arylthio- and Arylseleno-Substituted s-Heptazines
Uwe Böhme, Carl-Christoph Höhne, Christian Posern, Jörg Wagler, Edwin Kroke
In contrast to numerous thio- and selenocyanuric acid derivatives, sulfur- or selenium-containing s-heptazines have not been reported so far. Thio- and selenocyameluric acid esters were obtained by substitution reactions of s-heptazine chloride C6N7Cl3 with aromatic thiols and selenophenol; the resultant white or yellow solids were stable in air. They were comprehensively characterized by elemental analysis, 1H, 13C NMR, and IR spectroscopy. The thiocyameluric acid phenyl ester (1, C6N7(S(C6H5))3) and the corresponding selenium compound (7) formed co-crystals with mesitylene, which were analyzed by single-crystal X-ray diffraction. Both structures showed unusually large channels of ≈12 Å diameter. The thermal stability was measured by TGA (thermogravimetric analysis), and the flame retardancy of compound 1 was tested in PP by carrying out limiting oxygen index (LOI) measurements, which gave promising results. Quantum chemical calculations of the title compounds were performed to explain the observed properties and structural characteristics. Flame retardant materials: The first sulfur- or selenium-containing s-heptazines have been synthesized. They show interesting mesoporous crystal structures, are air-stable and very temperature-stable, and display promising luminescence and flame retardant properties (see figure).

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/chem.201700645

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