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dc.contributor.authorKuntze, Kim
dc.contributor.authorViljakka, Jani
dc.contributor.authorTitov, Evgenii
dc.contributor.authorAhmed, Zafar
dc.contributor.authorKalenius, Elina
dc.contributor.authorSaalfrank, Peter
dc.contributor.authorPriimagi, Arri
dc.date.accessioned2021-12-15T13:22:52Z
dc.date.available2021-12-15T13:22:52Z
dc.date.issued2022
dc.identifier.citationKuntze, K., Viljakka, J., Titov, E., Ahmed, Z., Kalenius, E., Saalfrank, P., & Priimagi, A. (2022). Towards low-energy-light-driven bistable photoswitches : ortho-fluoroaminoazobenzenes. <i>Photochemical and Photobiological Sciences</i>, <i>21</i>(2), 159-173. <a href="https://doi.org/10.1007/s43630-021-00145-4" target="_blank">https://doi.org/10.1007/s43630-021-00145-4</a>
dc.identifier.otherCONVID_102384380
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/78993
dc.description.abstractThermally stable photoswitches that are driven with low-energy light are rare, yet crucial for extending the applicability of photoresponsive molecules and materials towards, e.g., living systems. Combined ortho-fluorination and -amination couples high visible light absorptivity of o-aminoazobenzenes with the extraordinary bistability of o-fluoroazobenzenes. Herein, we report a library of easily accessible o-aminofluoroazobenzenes and establish structure–property relationships regarding spectral qualities, visible light isomerization efficiency and thermal stability of the cis-isomer with respect to the degree of o-substitution and choice of amino substituent. We rationalize the experimental results with quantum chemical calculations, revealing the nature of low-lying excited states and providing insight into thermal isomerization. The synthesized azobenzenes absorb at up to 600 nm and their thermal cis-lifetimes range from milliseconds to months. The most unique example can be driven from trans to cis with any wavelength from UV up to 595 nm, while still exhibiting a thermal cis-lifetime of 81 days.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherSpringer
dc.relation.ispartofseriesPhotochemical and Photobiological Sciences
dc.rightsCC BY 4.0
dc.subject.otherphotochemistry
dc.titleTowards low-energy-light-driven bistable photoswitches : ortho-fluoroaminoazobenzenes
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202112155979
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineAnalyyttinen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineAnalytical Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange159-173
dc.relation.issn1474-905X
dc.relation.numberinseries2
dc.relation.volume21
dc.type.versionpublishedVersion
dc.rights.copyright© 2021 the Authors
dc.rights.accesslevelopenAccessfi
dc.subject.ysovalokemia
dc.subject.ysofluori
dc.subject.ysoaromaattiset yhdisteet
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p7201
jyx.subject.urihttp://www.yso.fi/onto/yso/p16439
jyx.subject.urihttp://www.yso.fi/onto/yso/p23502
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.1007/s43630-021-00145-4
jyx.fundinginformationH2020 European Research Council, 679646, Arri Priimägi, Luonnontieteiden ja Tekniikan Tutkimuksen Toimikunta, 321065, Graduate School, Tampere University, Deutsche Forschungsgemeinschaft, 454020933, Evgenii Titov
dc.type.okmA1


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