A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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 toimittajat: Hupatz, Henrik; Gaedke, Marius; Schröder, Hendrik, V.; Beerhues, Julia; Valkonen, Arto; Klautzsch, Fabian; Müller, Sebastian; Witte, Felix; Rissanen, Kari; Sarkar, Biprajit; et al.
Lehti tai sarja: Beilstein Journal of Organic Chemistry
ISSN: 1860-5397
eISSN: 1860-5397
Julkaisuvuosi: 2020
Volyymi: 16
Artikkelin sivunumerot: 2576-2588
Kustantaja: Beilstein Institut
Julkaisumaa: Saksa
Julkaisun kieli: englanti
DOI: https://doi.org/10.3762/bjoc.16.209
Julkaisun avoin saatavuus: Avoimesti saatavilla
Julkaisukanavan avoin saatavuus: Kokonaan 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-asiasanat: supramolekulaarinen kemia
Vapaat asiasanat: crown ether; isothermal titration calorimetry; redox chemistry; rotaxanes; supramolecular chemistry
Liittyvät organisaatiot
Hankkeet, joissa julkaisu on tehty
- Vankat S...I+...S-halogeenisidotut supramolekulaariset kokoonpanot (tutkimuskulut)
- Valkonen, Arto
- Suomen Akatemia
OKM-raportointi: Kyllä
Raportointivuosi: 2020
JUFO-taso: 1