Aqueous Assembly of Zwitterionic Daisy Chains

Aeschi, Yves and Drayss-Orth, Sylvie and Valasek, Michal and Haeussinger, Daniel and Mayor, Marcel. (2019) Aqueous Assembly of Zwitterionic Daisy Chains. Chemistry - A European Journal, 25 (1). pp. 285-295.

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Official URL: https://edoc.unibas.ch/75518/

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The synthesis and characterization of zwitterionic molecular [c2]‐ and [a2]‐daisy chains are described, relying on recognition of a positively charged cyclophane and a negatively charged oligo(phenylene‐ethynylene) (OPE) rod in aqueous medium. For this purpose, syntheses of an acetylene‐functionalized macrocyclic receptor and a water‐soluble OPE‐rod as the guest component are presented, from which a heteroditopic daisy chain monomer was prepared. This monomer aggregated strongly in water/methanol 4:1 and formed molecular daisy chains, which were isolated as interlocked species from a stoppering reaction at 1 mm concentration. The cyclic dimer [c2] was the main product with an isolated yield of 30 % and consisted of a mixture of diastereomers, as evidenced by 1H NMR spectroscopy.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Molecular Devices and Materials (Mayor)
05 Faculty of Science > Departement Chemie > Chemie > Nuclear Magnetic Resonance (Häussinger)
UniBasel Contributors:Mayor, Marcel and Drayss-Orth, Sylvie Carolin and Aeschi, Yves and Häussinger, Daniel
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:04 Mar 2020 14:38
Deposited On:21 Feb 2020 11:56

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