In:
European Journal of Inorganic Chemistry, Wiley, Vol. 2010, No. 34 ( 2010-12), p. 5416-5425
Abstract:
The reaction of the N ‐lithiated 3,6‐di‐ tert ‐butyl‐carbazole ( 2 ) with 2‐bromo‐1,3‐diethyl‐1,3,2‐benzodiazaborole ( 1a ) and 2‐bromo‐1,3‐diphenyl‐1,3,2‐benzodiazaborole ( 1b ) afforded the 2‐ N ‐carbazolyl‐functionalized benzodiazaboroles 3a and 3b as colourless solids in 77 and 73 % yield, respectively.Synthesis of 2[5′‐ N ‐carbazolyl‐2′‐thienyl]‐1,3‐diethyl‐1,3,2‐benzodiazaborole ( 5a ) was effected by lithiation of N ‐(2‐thienyl)carbazole ( 4 ) and subsequent reaction with equimolar amounts of 1a , and 5a was obtained in 68 % yield. Similarly,2[5′‐ N ‐carbazolyl‐2′‐thienyl]‐1,3‐diphenyl‐1,3,2‐benzodiazaborole ( 5b ) was prepared from lithiated 4 and 1b in 62 % yield. Compounds 3a , b and 5a , b are characterized by elemental analyses, IR and NMR spectroscopy ( 1 H, 11 B, 13 C) and mass spectrometry. The molecular structures of 3a and 5a were elucidated by X‐ray diffraction analysis. These borylated systems show intense blue luminescence. The spectroscopic results were reproduced by TD‐DFT calculations at the [B3LYP/6‐311G (d,p)] level of theory.
Type of Medium:
Online Resource
ISSN:
1434-1948
,
1099-0682
DOI:
10.1002/ejic.v2010.34
DOI:
10.1002/ejic.201000665
Language:
English
Publisher:
Wiley
Publication Date:
2010
detail.hit.zdb_id:
1475009-0
detail.hit.zdb_id:
1409951-2
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