Synthesis, structural characterization and fluorescence properties of organoselenium compounds bearing a ligand containing both bulky and nonbonding groups - The first observation of both intramolecular Se center dot center dot center dot N and Se center dot center dot center dot O interactions in a diselenide structure

Abstract

The synthesis of bis[3-(4,5-dihydro-4,4-dimethyl-1,3-oxazol-2-yl)-4-(3,5-dimethylphenyl)-2-naphthyl] diselenide, R2Se2 (4), was achieved by a facile ortholithiation route. Further reaction of the diselenide with a stoichiometric amount of SO2Cl2 or Br-2 afforded the corresponding selenenyl halides RSeX [X = Cl (5), X = Br (6)]. The novel selenenyl iodide RSeI (7), in which the selenium and iodine are covalently bonded to each other, was obtained by treatment of the diselenide with an equimolar amount of iodine. The stable aryl benzyl selenide 8 was prepared by the reaction of benzyl chloride with lithium areneselenolate (3) at low temperature. Surprisingly, the reaction of the diselenide with 1,2-dibromo-o-xylene gave the selenenyl bromide (6) instead of the arylselenium derivative 9. Elemental analysis, multinuclear (H-1, C-13, Se-77) NMR spectroscopic and mass spectrometric techniques were used for the identification of products. Compounds 4, 6, 7, and 8 were also characterized by single-crystal X-ray diffraction studies. (C) Wiley-VCH Verlag GmbH Co.