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···N and Se···O interactions in a diselenide structure

Kandasamy, Karuppasamy ; Kumar, Sangit ; Singh, Harkesh B. ; Butcher, Ray J. ; Travis Holman, K. (2004) 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···N and Se···O interactions in a diselenide structure European Journal of Inorganic Chemistry, 2004 (5). pp. 1014-1023. ISSN 1434-1948

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Official URL: http://onlinelibrary.wiley.com/doi/10.1002/ejic.20...

Related URL: http://dx.doi.org/10.1002/ejic.200300603

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 Br2 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 (1H, 13C, 77Se) 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.

Item Type:Article
Source:Copyright of this article belongs to John Wiley and Sons.
Keywords:Selenium; Intramolecular Coordination; X-ray Diffraction; Fluorescence
ID Code:47627
Deposited On:11 Jul 2011 13:41
Last Modified:11 Jul 2011 13:41

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