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- W3100048549 abstract "Development of interlocked molecular ring-on-thread architectures (rotaxanes) represents a central current topic in supramolecular chemistry. This thesis considers the multi-step synthesis of rotaxane subcomponents, notably electroactive macrocyclic components, and their assembly into interlocked molecular structures. Novel hydrogen-bonding 31- and 35-member rings comprising a bis(2,6-diamidopyridine) receptor motif and an electroactive unit, namely ferrocene or triphenylamine, were synthesized. These macrocycles were analyzed by cyclic voltammetry, single crystal X-ray diffraction analysis, as well as NMR spectroscopy and mass spectrometry. Host-guest interactions with a complementary 5,5’-diethylbarbituric acid (Barbital) as model guest were also studied by electronic absorption and 1H-NMR spectroscopic titrations. Binding affinities were correlated to molecular structure. Approaches to form 2rotaxanes, notably by employing an active metal template reaction, where the metal ion plays the dual role of template and catalyst, are described. In particular, the copper(I)-catalyzed Huisgen as well as Glaser coupling reactions were employed with a variety of bulky stopper groups. In a second complementary “clipping”-type approach to rotaxane formation, the electroactive ring was directly formed encircling the templating thread component. This methodology yielded two further novel [2]rotaxanes via a template-assisted five-component clipping reaction, one rotaxane integrating two ferrocene units while the other comprised two triphenylamine-like units. Single crystal X-ray diffraction studies confirmed the interlocked nature of the assemblies." @default.
- W3100048549 created "2020-11-23" @default.
- W3100048549 creator A5019813974 @default.
- W3100048549 date "2018-12-11" @default.
- W3100048549 modified "2023-09-23" @default.
- W3100048549 title "Synthesis of electroactive macrocycles and rotaxanes" @default.
- W3100048549 hasPublicationYear "2018" @default.
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