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Anion binding by fluorescent ureido-hexahomotrioxacalix[3]arene receptors: An NMR, absorption and emission spectroscopic study.
Molecules 27:3247 (2022)
Fluorescent receptors (4a-4c) based on (thio)ureido-functionalized hexahomotrioxacalix[3]arenes were synthesised and obtained in the partial cone conformation in solution. Naphthyl or pyrenyl fluorogenic units were introduced at the lower rim of the calixarene skeleton via a butyl spacer. The binding of biologically and environmentally relevant anions was studied with NMR, UV-vis absorption, and fluorescence titrations. Fluorescence of the pyrenyl receptor 4c displays both monomer and excimer fluorescence. The thermodynamics of complexation was determined in acetonitrile and was entropy-driven. Computational studies were also performed to bring further insight into the binding process. The data showed that association constants increase with the anion basicity, and AcO-, BzO- and F- were the best bound anions for all receptors. Pyrenylurea 4c is a slightly better receptor than naphthylurea 4a, and both are more efficient than naphthyl thiourea 4b. In addition, ureas 4a and 4c were also tested as ditopic receptors in the recognition of alkylammonium salts.
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Publication type
Article: Journal article
Document type
Scientific Article
Keywords
Hexahomotrioxacalix[3]arenes ; Fluorescent Anion Receptors ; Nmr Studies ; Uv-vis Absorption Studies ; Fluorescence Studies ; Theoretical Calculations
ISSN (print) / ISBN
1420-3049
e-ISSN
1420-3049
Journal
Molecules
Quellenangaben
Volume: 27,
Issue: 10,
Article Number: 3247
Publisher
MDPI
Publishing Place
Basel
Non-patent literature
Publications
Reviewing status
Peer reviewed
Institute(s)
Institute of Structural Biology (STB)
Grants
Fundação para a Ciência e Tecnologia