Syntheses, Structure, Electrochemistry, and Optical Properties of 1,3-Diethyl-2,3-dihydro-1-H-1,3,2-pyrido-[4,5-b]-diazaboroles

Reaction of 2,5‐bis(dibromoboryl)thiophene (4) or 1,4‐bis(dibromoboryl)benzene (6) with two equivalents of N,N′‐dilithiated 2,3‐diaminopyridine (3) led to the generation of the pyridodiazaboroles 5 and 7 in which the two diazaborole rings are linked by 2,5‐thiophen‐diyl or 1,4‐phenylene units via th...

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Bibliographic Details
Published in:Zeitschrift für anorganische und allgemeine Chemie (1950) 2008-08, Vol.634 (10), p.1729-1734
Main Authors: Weber, L., Kahlert, J., Stammler, H.-G., Neumann, B.
Format: Article
Language:English
Subjects:
Boron
Cyclovoltammetry
Diazaboroles
Luminescence
Pyridines
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Summary:Reaction of 2,5‐bis(dibromoboryl)thiophene (4) or 1,4‐bis(dibromoboryl)benzene (6) with two equivalents of N,N′‐dilithiated 2,3‐diaminopyridine (3) led to the generation of the pyridodiazaboroles 5 and 7 in which the two diazaborole rings are linked by 2,5‐thiophen‐diyl or 1,4‐phenylene units via the boron atom. The novel compounds were characterized by elemental analyses and spectroscopy (1H‐, 11B‐, 13C‐NMR, MS, and UV‐VIS). The molecular structure of 5 was elucidated by X‐ray diffraction. Cyclovoltammograms of 5 and 7 show two irreversible oxidation waves at 0.76 and 0.73 V, respectively vs Fc/Fc+. The novel compounds display intense blue luminescence with Stokes shifts of 76 and 74 nm and relative quantum yields of 39 and 43 % vs Coumarin 120 (Φ = 50 %).
ISSN:0044-2313
1521-3749
DOI:10.1002/zaac.200800157