Synthesis and Properties of Cycloparaphenylene-2,5-pyridylidene: A Nitrogen-Containing Carbon Nanoring

The first synthesis of a nitrogen-containing cycloparaphenylene, cyclo[14]paraphenylene[4]2,5-pyridylidene ([14,4]CPPy), has been achieved. A palladium-catalyzed stepwise assembly of 2,2'-bipyridine, benzene, and L-shaped cyclohexane units, followed by NaHSO4/o-chloranil-mediated aromatization, successfully provided [14,4]CPPy. While the absorption and fluorescence properties of [14,4]CPPy were somewhat similar to those of cycloparaphenylenes (lambda(abs) = 344 nm, epsilon = 7.3 x 10(4) cm(-1) M-1, lambda(em) = 427 nm, Phi(F) = 0.80), it was found that [14,4]CPPy possesses an interesting halochromic property.