Journal
TETRAHEDRON LETTERS
Volume 48, Issue 26, Pages 4471-4475Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2007.05.008
Keywords
basicity; UV-vis absorption spectrum; emission spectrum; cross-coupling reaction; metal complexation
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The title azaazulene 3 was synthesized either by reaction of tropone with N-{(2-pyridyl)acetyl}pyridinium iodide in the presence of ammonium acetate or by palladium-catalyzed cross-coupling between 2-halo-1-azaazulene and 2-substituted pyridine. The compound shows relatively stronger basicity compared with 2,2'-bipyridyl. While 3 showed no emission from the S-1 state but from the S-2 state like azulene does, the protonated species of 3 exhibited emission from the S-1 state. Cationic metal-dependent absorption and emission relating to complexation were also studied. (c) 2007 Elsevier Ltd. All rights reserved.
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