The focus of the title work is on the selective and stepwise attachment of functional pyridine and bipyridine (bpy) groups at the 1,3, and 6 positions of the pentafulvene core. Reaction of 1,3-diphenylcyclopentadiene with 4-alkynylbenzaldehyde (EtOH/pyrrolidine) gave 1,3-diphenyl-6-(p-alkynylphenyl)fulvene 1  as a dark red solid. Sonagashira coupling of 1  with 5-bromo-2,2'-bipyridine gave the monosubstituted bpy-fulvene compound 2  . Entry into the synthetic strategy for (bis) bpy fulvenes, in which the bpy is directly attached to the fulvene core, has also been developed using 3-Ph and 3-(p-bromo)Ph 2-cyclopentene-1-ones as starting materials. The reactivity of the lithium reagent as well as the Mg and Ca Grignard reagents of 5-bromo-2,2'-bipyridine with the 3-Ph and 3-(p-bromo)Ph cyclopenteneones will be compared. Reaction of the bpy cyclopentadienes obtained from this strategy with 2,2'-bipyridine-5-carbaldehyde or 2,2'-bipyridine-4-carbaldehyde (EtOH/pyrrolidine) as well as the coordination chemistry and structure property relationships of the resulting new bpy-fulvene compounds will also be presented.

Bipyridine decorated fulvenes: New ligands and functional materials for organic electronics

247th National Meeting (2014)

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