Photoswitchable hydrazones with pyridine-based rotors and halogen substituents

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dc.contributor.authorKotásková, Luciecs
dc.contributor.authorJewula, Pawelcs
dc.contributor.authorHerchel, Radovancs
dc.contributor.authorNemec, Ivancs
dc.contributor.authorNeugebauer, Petrcs
dc.coverage.issue29cs
dc.coverage.volume14cs
dc.date.accessioned2025-02-03T14:50:55Z
dc.date.available2025-02-03T14:50:55Z
dc.date.issued2024-06-27cs
dc.description.abstractThe Z,E-photoisomerization of pyridine-based hydrazone switches is typically suppressed due to the presence of pyridine-based rotors. The crystal structures of studied compounds were investigated using theoretical methods combining DFT and QT-AIM calculations to unveil the nature and properties of the intramolecular hydrogen bonding. In this study, we introduced a new series of pyridine-based hydrazones anchored with o-halogen substituents (2-X) and investigated their photoswitching abilities using 1H NMR and UV-Vis spectroscopy. The efficiency of the photoisomerization from initial 2-X-Z to the 2-X-E isomer varied, with the highest yield observed for 2-Cl-E (55%). Our findings, supported by DFT calculations, revealed the formation of a new diastereomer, 2-X-E*, upon back-photoisomerization. We demonstrated that hydrazones from the 2-X series can be reversibly photoswitched using irradiation from the UV-Vis range, and additionally, we explored the effect of the halogen atom on their switching capabilities and also on their thermodynamics and kinetics of photoswitching, determining their molecular solar thermal energy storage potential. We report on the E,Z-photoisomerization of hydrazone switches with pyridine-based rotors and halogen-substituted stators.en
dc.formattextcs
dc.format.extent20856-20866cs
dc.format.mimetypeapplication/pdfcs
dc.identifier.citationRSC Advances. 2024, vol. 14, issue 29, p. 20856-20866.en
dc.identifier.doi10.1039/d4ra02909gcs
dc.identifier.issn2046-2069cs
dc.identifier.orcid0000-0003-4825-3616cs
dc.identifier.orcid0000-0002-2586-7685cs
dc.identifier.orcid0000-0003-3231-7849cs
dc.identifier.orcid0000-0001-7095-6401cs
dc.identifier.other190011cs
dc.identifier.researcheridJ-5254-2018cs
dc.identifier.researcheridA-6969-2010cs
dc.identifier.researcheridI-7844-2013cs
dc.identifier.scopus24554099800cs
dc.identifier.scopus57201282084cs
dc.identifier.urihttps://hdl.handle.net/11012/249998
dc.language.isoencs
dc.publisherROYAL SOC CHEMISTRYcs
dc.relation.ispartofRSC Advancescs
dc.relation.urihttps://pubs.rsc.org/en/content/articlelanding/2024/ra/d4ra02909gcs
dc.rightsCreative Commons Attribution-NonCommercial 3.0 Unportedcs
dc.rights.accessopenAccesscs
dc.rights.sherpahttp://www.sherpa.ac.uk/romeo/issn/2046-2069/cs
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/cs
dc.subjectISOMERIZATION MECHANISMen
dc.subjectBASIS-SETSen
dc.subjectCRYSTALen
dc.subjectPHen
dc.titlePhotoswitchable hydrazones with pyridine-based rotors and halogen substituentsen
dc.type.driverarticleen
dc.type.statusPeer-revieweden
dc.type.versionpublishedVersionen
sync.item.dbidVAV-190011en
sync.item.dbtypeVAVen
sync.item.insts2025.02.03 15:50:55en
sync.item.modts2025.01.31 12:32:02en
thesis.grantorVysoké učení technické v Brně. Středoevropský technologický institut VUT. Magneto-Optická a THz Spektroskopiecs
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