Peripheral Modification of Tripodal Aza-Oxa-Crown Oxa-TriQuinoline

Oxa-TriQuinoline (o-TQ) is a new entry in the collection of aza-oxa-crown compounds featuring a semi-rigid flexible conformation and a tripodal ligation capability through three quinoline units. Herein, we describe the installation of functional groups and aromatic substituents on the outer edge of...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 2023-10, Vol.96 (10), p.1139-1143
Main Authors: Kobayashi, Toi, Sakurai, Takuya, Kumagai, Naoya
Format: Article
Language:English
Subjects:
Crystallography
Functional groups
Photoluminescence
Quinoline
Solid state
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Summary:Oxa-TriQuinoline (o-TQ) is a new entry in the collection of aza-oxa-crown compounds featuring a semi-rigid flexible conformation and a tripodal ligation capability through three quinoline units. Herein, we describe the installation of functional groups and aromatic substituents on the outer edge of o-TQ to modulate its physicochemical properties. Amino and bromo substituents were regioselectively introduced at the 5-position, forming bowl-shaped Cu(I) complexes in which three quinoline units coordinated to Cu(I). X-ray crystallography indicated that these o-TQ derivatives preferred an almost identical geometry in both the absence and presence of Cu(I). In contrast to o-TQ, some new o-TQ derivatives exhibited photoluminescent properties in solution and/or in the solid state depending on the substituents.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.20230184