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2018-05-14Zeitschriftenartikel DOI: 10.18452/19699
Sensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
dc.contributor.authorFredrich, Sebastian
dc.contributor.authorBonasera, Aurelio
dc.contributor.authorValderrey, Virginia
dc.contributor.authorHecht, Stefan
dc.date.accessioned2019-02-06T10:34:31Z
dc.date.available2019-02-06T10:34:31Z
dc.date.issued2018-05-14
dc.identifier.urihttp://edoc.hu-berlin.de/18452/20483
dc.description.abstractUpon light-induced isomerization, diarylethenes (DAEs) equipped with reactive aldehyde moieties rearrange selectively in the presence of amines, accompanied by decoloration. In a comprehensive study, the probe structure was optimized with regard to its inherent reactivity in the nucleophile-triggered rearrangement reaction. Detailed structure−reactivity relationships could be derived, in particular with regard to the type of integrated (het)aryl moieties as well as the location of the formyl residue, and the probes’ intrinsic reactivity with primary and secondary amines was optimized. Utilizing an ancillary base, the initially formed rearrangement product can engage in a subsequent catalytic cycle, leading to an amplified decoloration process. This additional catalytic pathway allows us to enhance the sensitivity of our method and successfully discriminate between amines and thiols. Moreover, probes that exhibit strong analyte-induced fluorescence modulation have been designed to further decrease the detection limit by using a more sensitive read-out. The optimized DAE probes are promising molecular components for future programmable sensing materials and devices.eng
dc.language.isoeng
dc.publisherHumboldt-Universität zu Berlin
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subject.ddc547 Organische Chemie
dc.subject.ddc541 Physikalische Chemie
dc.subject.ddc540 Chemie und zugeordnete Wissenschaften
dc.titleSensitive Assays by Nucleophile-Induced Rearrangement of Photoactivated Diarylethenes
dc.typearticle
dc.identifier.urnurn:nbn:de:kobv:11-110-18452/20483-6
dc.identifier.doihttp://dx.doi.org/10.18452/19699
dc.type.versionpublishedVersion
local.edoc.pages9
local.edoc.type-nameZeitschriftenartikel
local.edoc.container-typeperiodical
local.edoc.container-type-nameZeitschrift
dc.description.versionPeer Reviewed
dcterms.bibliographicCitation.doi10.1021/jacs.8b02982
dcterms.bibliographicCitation.journaltitleJournal of the American Chemical Society
dcterms.bibliographicCitation.volume140
dcterms.bibliographicCitation.issue20
dcterms.bibliographicCitation.originalpublishernameAmerican Chemical Society
dcterms.bibliographicCitation.originalpublisherplaceWashington, DC
dcterms.bibliographicCitation.pagestart6432
dcterms.bibliographicCitation.pageend6440
bua.departmentMathematisch-Naturwissenschaftliche Fakultät

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