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

Bibliographic Details
Main Author: Spirache, Maria Angela
Publication Date: 2023
Other Authors: Marrec, Philippe, Dias Parola, António Jorge, Tonicha Laia, César António
Format: Article
Language: eng
Source: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Download full: http://hdl.handle.net/10362/154572
Summary: Publisher Copyright: © 2023 The Author(s)
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spelling Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyesChromogenic dyesFlavyliumLeuco dyesReversibilitySpirolactone dyesThermochromismChemical Engineering(all)Process Chemistry and TechnologyPublisher Copyright: © 2023 The Author(s)The 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.DQ - Departamento de QuímicaLAQV@REQUIMTERUNSpirache, Maria AngelaMarrec, PhilippeDias Parola, António JorgeTonicha Laia, César António2023-06-28T22:19:19Z2023-062023-06-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article9application/pdfhttp://hdl.handle.net/10362/154572eng0143-7208PURE: 64823534https://doi.org/10.1016/j.dyepig.2023.111208info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-03-11T05:37:01Zoai:run.unl.pt:10362/154572Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:55:40.783565Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
title Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
spellingShingle Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
Spirache, Maria Angela
Chromogenic dyes
Flavylium
Leuco dyes
Reversibility
Spirolactone dyes
Thermochromism
Chemical Engineering(all)
Process Chemistry and Technology
title_short Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
title_full Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
title_fullStr Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
title_full_unstemmed Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
title_sort Reversible thermochromic systems based on a new library of flavylium spirolactone leuco dyes
author Spirache, Maria Angela
author_facet Spirache, Maria Angela
Marrec, Philippe
Dias Parola, António Jorge
Tonicha Laia, César António
author_role author
author2 Marrec, Philippe
Dias Parola, António Jorge
Tonicha Laia, César António
author2_role author
author
author
dc.contributor.none.fl_str_mv DQ - Departamento de Química
LAQV@REQUIMTE
RUN
dc.contributor.author.fl_str_mv Spirache, Maria Angela
Marrec, Philippe
Dias Parola, António Jorge
Tonicha Laia, César António
dc.subject.por.fl_str_mv Chromogenic dyes
Flavylium
Leuco dyes
Reversibility
Spirolactone dyes
Thermochromism
Chemical Engineering(all)
Process Chemistry and Technology
topic Chromogenic dyes
Flavylium
Leuco dyes
Reversibility
Spirolactone dyes
Thermochromism
Chemical Engineering(all)
Process Chemistry and Technology
description Publisher Copyright: © 2023 The Author(s)
publishDate 2023
dc.date.none.fl_str_mv 2023-06-28T22:19:19Z
2023-06
2023-06-01T00:00:00Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10362/154572
url http://hdl.handle.net/10362/154572
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0143-7208
PURE: 64823534
https://doi.org/10.1016/j.dyepig.2023.111208
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 9
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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