Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes
Hupatz, H., Gaedke, M., Schröder, H., Beerhues, J., Valkonen, A., Klautzsch, F., Müller, S., Witte, F., Rissanen, K., Sarkar, B., & Schalley, C. A. (2020). Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes. Beilstein Journal of Organic Chemistry, 16, 2576-2588. https://doi.org/10.3762/bjoc.16.209
Julkaistu sarjassa
Beilstein Journal of Organic ChemistryTekijät
Päivämäärä
2020Tekijänoikeudet
© 2020 Hupatz et al.; licensee Beilstein-Institut
Crown ethers are common building blocks in supramolecular chemistry and are frequently applied as cation sensors or as subunits in synthetic molecular machines. Developing switchable and specifically designed crown ethers enables the implementation of function into molecular assemblies. Seven tailor-made redox-active crown ethers incorporating tetrathiafulvalene (TTF) or naphthalene diimide (NDI) as redox-switchable building blocks are described with regard to their potential to form redox-switchable rotaxanes. A combination of isothermal titration calorimetry and voltammetric techniques reveals correlations between the binding energies and redox-switching properties of the corresponding pseudorotaxanes with secondary ammonium ions. For two different weakly coordinating anions, a surprising relation between the enthalpic and entropic binding contributions of the pseudorotaxanes was discovered. These findings were applied to the synthesis of an NDI-[2]rotaxane, which retains similar spectroelectrochemical properties compared to the corresponding free macrocycle. The detailed understanding of the thermodynamic and electrochemical properties of the tailor-made crown ethers lays the foundation for the construction of new types of molecular redox switches with emergent properties.
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Julkaisija
Beilstein InstitutISSN Hae Julkaisufoorumista
1860-5397Asiasanat
Julkaisu tutkimustietojärjestelmässä
https://converis.jyu.fi/converis/portal/detail/Publication/42893129
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Suomen AkatemiaRahoitusohjelmat(t)
Akatemiatutkijan tutkimuskulut, SALisätietoja rahoituksesta
This research was funded by the Deutsche Forschungsgemeinschaft and the Academy of Finland (decision no. 314343).Lisenssi
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