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Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes (2020)


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


JYU-tekijät tai -toimittajat


Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajatHupatz, Henrik; Gaedke, Marius; Schröder, Hendrik, V.; Beerhues, Julia; Valkonen, Arto; Klautzsch, Fabian; Müller, Sebastian; Witte, Felix; Rissanen, Kari; Sarkar, Biprajit; et al.

Lehti tai sarjaBeilstein Journal of Organic Chemistry

ISSN1860-5397

eISSN1860-5397

Julkaisuvuosi2020

Volyymi16

Artikkelin sivunumerot2576-2588

KustantajaBeilstein Institut

JulkaisumaaSaksa

Julkaisun kielienglanti

DOIhttps://doi.org/10.3762/bjoc.16.209

Julkaisun avoin saatavuusAvoimesti saatavilla

Julkaisukanavan avoin saatavuusKokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX)https://jyx.jyu.fi/handle/123456789/72284


Tiivistelmä

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.


YSO-asiasanatsupramolekulaarinen kemia

Vapaat asiasanatcrown ether; isothermal titration calorimetry; redox chemistry; rotaxanes; supramolecular chemistry


Liittyvät organisaatiot

JYU-yksiköt:


Hankkeet, joissa julkaisu on tehty


OKM-raportointiKyllä

Raportointivuosi2020

JUFO-taso1


Viimeisin päivitys 2024-26-03 klo 09:19