Oxa‐TriQuinoline: A New Entry to Aza‐Oxa‐Crown Architectures**

Author:

Kobayashi Toi1ORCID,Kumagai Naoya12ORCID

Affiliation:

1. Graduate School of Pharmaceutical Sciences Keio University 1-5-30 Shibakoen, Minato-ku Tokyo 105-8512 Japan

2. Institute of Microbial Chemistry 3-14-23 Kamiosaki, Shinagawa-ku Tokyo 141-0021 Japan

Abstract

AbstractA 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 SNAr reactions, giving rise to the characteristic N3O3 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.

Funder

Japan Society for the Promotion of Science

Publisher

Wiley

Subject

General Medicine

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