A BN‐Doped Cycloparaphenylene Debuts

2020 
The 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.
    • Correction
    • Source
    • Cite
    • Save
    • Machine Reading By IdeaReader
    56
    References
    8
    Citations
    NaN
    KQI
    []