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A BN‐Doped Cycloparaphenylene Debuts

Abstract : 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.
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Submitted on : Monday, December 7, 2020 - 11:28:47 AM
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Min Chen, Kiran Unikela, Rongala Ramalakshmi, Bo Li, Clovis Darrigan, et al.. A BN‐Doped Cycloparaphenylene Debuts. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2021, 60 (3), pp.1556-1560. ⟨10.1002/anie.202010556⟩. ⟨hal-03043314⟩



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