Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures.

A new 15-membered-macrocyclic molecular entity, oxa-TriQuinoline (o-TQ), was designed and synthesized. In o-TQ, three oxygen atoms were joined onto three quinoline units at the 2- and 8-positions in a head-to-tail fashion by three-fold SN Ar reactions, giving rise to the characteristic N3 O3 aza-oxa-crown architecture. o-TQ can serve as a new tridentate nitrogen ligand to capture a CuI cation and adopt a bowl shape, before supramolecular complexation with corannulene and [12]cycloparaphenylene (CPP) occurs through π-π and CH-π interactions. In the presence of the CuI cation, the non-emissive o-TQ becomes a highly emissive material in the solid state, whereby the emission wavelengths depend on the ancillary ligand on the CuI cation. The o-TQ/CuI complex is able to promote carbene catalysis to provide a range of enamines with a gem-difluorinated terminus. © 2023 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.

Citation

Toi Kobayashi, Naoya Kumagai. Oxa-TriQuinoline: A New Entry to Aza-Oxa-Crown Architectures. Angewandte Chemie (International ed. in English). 2023 Aug 07;62(32):e202307896

PMID: 37337998

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