We present an in-depth investigation of cyclodextrin complexes with guest compounds featuring complexation-induced room temperature phosphorescence (RTP) in aqueous solution. Very interestingly, only the complexed regioisomers bearing lateral substituents on meta-position show RTP, whereas the stronger host-guest systems with para-substituted dyes show no RTP features. The reported systems were investigated regarding their complexation behavior in water using isothermal titration calorimetry and mass spectrometry. In the case of γ-CD very strong 1 : 1 inclusion complexes (Ka up to 5.13×105 M−1) were unexpectedly observed. It was found that not only a strong binding to the cyclodextrin cavity is needed to restrict motion, inducing the emission, but also the conformation inside the cavity plays a pivotal role – as supported by an extensive NMR study and MD simulations.

Phosphorescence Induction by Host-Guest Complexation with Cyclodextrins - The Role of Regioisomerism and Affinity / M. Hayduk, T. Schaller, F.C. Niemeyer, K. Rudolph, G.H. Clever, F. Rizzo, J. Voskuhl. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 28:51(2022), pp. e202201081.1-e202201081.11. [10.1002/chem.202201081]

Phosphorescence Induction by Host-Guest Complexation with Cyclodextrins - The Role of Regioisomerism and Affinity

F. Rizzo
Co-ultimo
;
2022

Abstract

We present an in-depth investigation of cyclodextrin complexes with guest compounds featuring complexation-induced room temperature phosphorescence (RTP) in aqueous solution. Very interestingly, only the complexed regioisomers bearing lateral substituents on meta-position show RTP, whereas the stronger host-guest systems with para-substituted dyes show no RTP features. The reported systems were investigated regarding their complexation behavior in water using isothermal titration calorimetry and mass spectrometry. In the case of γ-CD very strong 1 : 1 inclusion complexes (Ka up to 5.13×105 M−1) were unexpectedly observed. It was found that not only a strong binding to the cyclodextrin cavity is needed to restrict motion, inducing the emission, but also the conformation inside the cavity plays a pivotal role – as supported by an extensive NMR study and MD simulations.
cyclodextrins; host-guest systems; isothermal titration calorimetry; room temperature phosphorescence; supramolecular chemistry
Settore CHEM-05/A - Chimica organica
Settore CHEM-06/A - Fondamenti chimici delle tecnologie
2022
Article (author)
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/1106688
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