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Syntheses, Structure, Electrochemistry, and Optical Properties of 1,3‐Diethyl‐2,3‐dihydro‐1‐ H ‐1,3,2‐pyrido‐[4,5‐b]‐diazaboroles
Author(s) -
Weber L.,
Kahlert J.,
Stammler H.G.,
Neumann B.
Publication year - 2008
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200800157
Subject(s) - chemistry , benzene , boron , electrochemistry , thiophene , spectroscopy , luminescence , phenylene , nuclear magnetic resonance spectroscopy , medicinal chemistry , elemental analysis , crystallography , stereochemistry , organic chemistry , materials science , polymer , physics , optoelectronics , electrode , quantum mechanics
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 ( 1 H‐, 11 B‐, 13 C‐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 %).