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Synthesis and properties of 2-(2-pyridyl)-1-azaazulene

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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 diprotonated species of 3, generated in 50% H_2SO_4 exhibited emission from the S_1 state. Cationic metal-dependent absorption and emission were also studied.

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