A BN‐Doped Cycloparaphenylene Debuts

Abstract

AbstractThe first example of a BN‐doped cycloparaphenylene BN‐[10]CPP was synthesized and characterized. Its reactivity and photophysical properties were evaluated in direct comparison to its carbonaceous analogues Mes‐[10]CPP and [10]CPP. While the photophysical properties of BN‐[10]CPP remains similar to its carbonaceous analogues, the electronic structure changes associated with the introduction of a 1,2‐azaborine BN heterocycle into a CPP scaffold enables facile and selective late‐stage functionalizations that cannot be accomplished with carbonaceous CPPs. Specifically, Ir‐catalyzed hydrogenation of BN‐[10]CPP selectively reduces the BN heterocyclic ring, which upon hydrolysis produces a rare example of a macrocyclic paraphenylene 6 incorporating the versatile ketone functionality within the macrocyclic ring.