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Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes

2023-06Artigo científico Acesso aberto
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dc.contributor.authorSpirache, Maria Angela
dc.contributor.authorMarrec, Philippe
dc.contributor.authorDias Parola, António Jorge
dc.contributor.authorTonicha Laia, César António
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.pblElsevier
dc.date.accessioned2023-06-28T22:19:19Z
dc.date.available2023-06-28T22:19:19Z
dc.date.issued2023-06
dc.descriptionPublisher Copyright: © 2023 The Author(s)
dc.description.abstractThe aim of this work was the design, synthesis, and characterization of new chromogenic spirolactone dyes based on a 2-phenyl-1-benzopyrylium (flavylium) backbone for further development of thermochromic smart labels. The influence of electron-donating and electron-withdrawing groups on the five synthesized dyes was studied in terms of color modification, acid-base behavior and thermochromic properties. By using UV–Vis absorption and emission spectroscopies, molar absorptivity, oscillator strength, Stokes shift, and fluorescence quantum yield were determined for each dye to evaluate the impact on color and excited state properties of the designed structures. The acid-base behavior and the ability to evolve towards leuco species was assessed by titrations with triethylamine and N,N-diisopropylethylamine in non-polar and polar aprotic solvents such as acetonitrile and octan-1-ol. In addition, the reversibility of the color was also evaluated by titrations with polar protic solvents (water and ethanol) and Lewis acids (gallic acid and iron(III) chloride). The number of equivalents of base/acid required to reach the leuco product and then to reverse the color were determined by representing the absorption maximum as a function of added base/acid in acetonitrile (water content less than 0.01-v/v). Finally, the thermochromic properties were evaluated in the presence of long-chain organic amines and water-insoluble solvents with melting points close to room temperature. The synthesized compounds can switch between two species if the appropriate conditions are used. Moreover, the tests carried out to assess their thermochromic behavior concluded that all dyes display thermochromism to some extent. The dyes that have electron-withdrawing groups attached, such as cyano, display stronger chromogenic effects useful for future applications.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent9
dc.format.extent3466126
dc.identifier.doi10.1016/j.dyepig.2023.111208
dc.identifier.issn0143-7208
dc.identifier.otherPURE: 64823534
dc.identifier.otherPURE UUID: 19aaabb5-337a-48ee-b90a-f3bbb9f9b285
dc.identifier.otherScopus: 85149441657
dc.identifier.otherWOS: 000952195700001
dc.identifier.otherORCID: /0000-0002-1333-9076/work/151366883
dc.identifier.otherORCID: /0000-0001-6410-6072/work/151409191
dc.identifier.urihttp://hdl.handle.net/10362/154572
dc.identifier.urlhttps://www.scopus.com/pages/publications/85149441657
dc.language.isoeng
dc.peerreviewedyes
dc.relationinfo:eu-repo/grantAgreement/EC/H2020/814299/EU
dc.relationENTREPRENEURING CHEMICAL IRREVERSIBILITY TO PROTOTYPE RESPONSIVE SMART LABELS
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.subjectChromogenic dyes
dc.subjectFlavylium
dc.subjectLeuco dyes
dc.subjectReversibility
dc.subjectSpirolactone dyes
dc.subjectThermochromism
dc.subjectGeneral Chemical Engineering
dc.subjectProcess Chemistry and Technology
dc.titleReversible thermochromic systems based on a new library of flavylium spirolactone leuco dyesen
dc.typejournal article
degois.publication.titleDyes and Pigments
degois.publication.volume214
dspace.entity.typePublication
oaire.awardNumber814299
oaire.awardNumberUIDB/50006/2020
oaire.awardTitleENTREPRENEURING CHEMICAL IRREVERSIBILITY TO PROTOTYPE RESPONSIVE SMART LABELS
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/EC/H2020/814299/EU
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.fundingStreamH2020
oaire.fundingStream6817 - DCRRNI ID
project.funder.identifierhttp://doi.org/10.13039/501100008530
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameEuropean Commission
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
relation.isProjectOfPublicationd3c601e5-b4c1-4dab-ac4f-480f52f54f8c
relation.isProjectOfPublicationadc84c24-ba1d-4bcd-b753-2128ce9a5faa
relation.isProjectOfPublication.latestForDiscoveryadc84c24-ba1d-4bcd-b753-2128ce9a5faa

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