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

Creators Oda Mitsunori

Creators Ogura Kazutaka

Creators Chung Thanh Nguyen

Creators Kishi Sayaka

Creators Kuroda Shigeyasu

Creators Fujimori Kunihide

Creators Noda Tomonori

Creators Abe Noritaka

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.

[ISSN]0040-4039

[NCID]AA00861801

https://doi.org/10.1016/j.tetlet.2007.05.008

[isVersionOf] [URI]http://www.sciencedirect.com/science/journal/00404039