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Journal Articles Angewandte Chemie International Edition Year : 2021

A BN‐Doped Cycloparaphenylene Debuts

Min Chen
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  • PersonId : 755831
  • IdRef : 135605172
Kiran Unikela
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Rongala Ramalakshmi
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Bo Li
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  • IdRef : 153351551
Shih‐yuan Liu
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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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Dates and versions

hal-03043314 , version 1 (20-12-2023)

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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, 2021, 60 (3), pp.1556-1560. ⟨10.1002/anie.202010556⟩. ⟨hal-03043314⟩
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