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A study of azopyrimidine photoswitches and their interactions with cyclodextrins: When the guest governs the type of accommodation at the host
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SYSNO ASEP 0567686 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title A study of azopyrimidine photoswitches and their interactions with cyclodextrins: When the guest governs the type of accommodation at the host Author(s) Hruzíková, Anna (UOCHB-X) ORCID
Mužíková Čechová, Lucie (UOCHB-X) ORCID, RID
Štěpánová, Sille (UOCHB-X) ORCID
Tučková, Lucie (UOCHB-X) ORCID
Tichotová, Markéta (UOCHB-X) ORCID
Růžička, A. (CZ)
Kašička, Václav (UOCHB-X) RID, ORCID
Procházková, Eliška (UOCHB-X) RID, ORCIDArticle number 111099 Source Title Dyes and Pigments. - : Elsevier - ISSN 0143-7208
Roč. 212, April (2023)Number of pages 10 s. Language eng - English Country GB - United Kingdom Keywords intramolecular hydrogen bonds ; cis-trans isomerization ; β-cyclodextrin OECD category Analytical chemistry R&D Projects GA20-03899S GA ČR - Czech Science Foundation (CSF) Research Infrastructure e-INFRA CZ - 90140 - CESNET, zájmové sdružení právnických osob Method of publishing Limited access Institutional support UOCHB-X - RVO:61388963 UT WOS 000921063400001 EID SCOPUS 85146436530 DOI 10.1016/j.dyepig.2023.111099 Annotation Azopyrimidines have recently emerged as a new class of photoswitches structurally similar to azobenzenes switching between trans and cis isomers. These compounds have a wide range of potential applications in photopharmacology, catalysis or as molecular devices, but their low solubility in water limits their biological applications. Nevertheless, this drawback could be overcome by their inclusion into supramolecular structures. To test this hypothesis, we prepared a series of azopyrimidines and investigated their structure, cis-trans isomerization and host-guest chemistry with cyclodextrins (CDs) using an experimental-theoretical approach combining capillary electrophoresis (CE), Nuclear Magnetic Resonance (NMR) spectroscopy and computational models. The results revealed that β-CD exhibits high selectivity over several CDs tested for the accommodation of the studied compounds. Orientation of guests in inclusion complexes was experimentally assessed by Nuclear Overhauser Effect (NOE) contacts and supported by quantum-chemical calculations. Moreover, investigation of noncovalent interactions of azopyrimidines with β-CD by CE showed that azopyrimidines with suitable structural modification can form strong complexes with high values of binding constants (over 17 000 L mol−1). For such complexes, trans-cis isomerization proceeds directly inside the β-CD cavity with azopyrimidine remaining encapsulated through its narrower primary portal. By contrast, in weakly interacting complexes, the trans isomer is released, and the cis isomer is generated outside the cavity. In subsequent re-complexation, the cis isomer is then re-captured through the wider secondary portal. Therefore, our findings point to two significantly different complexation processes depending on substitutional pattern and binding constant values of azopyrimidines, a feature which may lead to future promising applications. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2024 Electronic address https://doi.org/10.1016/j.dyepig.2023.111099
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