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Exploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCs

2023-10Artigo científico Acesso aberto
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dc.contributor.authorPinto, Ana Lúcia
dc.contributor.authorMáximo, Patrícia
dc.contributor.authorPina, João
dc.contributor.authorCalogero, Giuseppe
dc.contributor.authorLaia, César A. T.
dc.contributor.authorParola, A. Jorge
dc.contributor.authorLima, J. Carlos
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.pblElsevier
dc.date.accessioned2023-08-21T22:18:02Z
dc.date.available2023-08-21T22:18:02Z
dc.date.issued2023-10
dc.descriptionPublisher Copyright: © 2023 The Authors
dc.description.abstractSharing with anthocyanins the 2-phenyl-1-benzopyrylium structural motif, flavylium derivatives are strongly colored bio-inspired dyes that have been explored in dye-sensitized solar cells (DSSCs). Following on the fact that the most efficient flavylium-based dyes for DSSCs require amine electron-donating groups, a diethylamino group and the corresponding rigidified julolidine group were introduced in the benzopyrylium core. This structural variation was combined with another structural parameter – increased planarization of the flavylium ring system – to yield four flavylium derivatives all with a catechol anchoring group. The several pKa values of the new dyes and the UV–vis absorption data at different pH values and upon adsorption to TiO2 (corroborated by TD-DFT calculations) demonstrate a stronger delocalization of the nitrogen lone pair in the julolidine systems when compared to the diethylamino ones, reflecting the stronger electron-donating ability of the former. However, the julolidine-based dyes resulted in a decrease in all DSSC parameters, with efficiencies of 0.6% vs. 2.3% for the diethylamino devices. Discarding eventual increased self-aggregation processes of the more planar julolidine derivatives through studies with a de-aggregating agent (CDCA), and determining comparable dye loadings for all dyes, the presence of increased back-electron transfer processes for the julolidine-based compounds is advanced to explain their lower efficiencies. Rigidification of the flavylium dyes by bridging the benzopyrylium and the phenyl rings is demonstrated by higher fluorescence quantum yields and by electrochemical data and leads to a slight increase in the efficiency of the respective DSSCs. The results contribute to consolidate the potential of flavylium dyes as sensitizers for DSSCs.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent12
dc.format.extent4766169
dc.identifier.doi10.1016/j.dyepig.2023.111495
dc.identifier.issn0143-7208
dc.identifier.otherPURE: 68027564
dc.identifier.otherPURE UUID: cc612b5a-094c-4e48-9772-56c7e832c456
dc.identifier.otherScopus: 85164215811
dc.identifier.otherWOS: 001037803200001
dc.identifier.otherORCID: /0000-0002-1333-9076/work/151366884
dc.identifier.otherORCID: /0000-0003-0528-1967/work/151391645
dc.identifier.otherORCID: /0000-0001-6410-6072/work/151409193
dc.identifier.urihttp://hdl.handle.net/10362/156749
dc.identifier.urlhttps://www.scopus.com/pages/publications/85164215811
dc.language.isoeng
dc.peerreviewedyes
dc.relationFunding Information: info:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationTriplet States of Flavylium Dyes in Smart Textile Photovoltaics
dc.relationCoimbra Chemistry Center
dc.relationCoimbra Chemistry Center
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00313%2F2020/PT
dc.subjectBio-inspired dyes
dc.subjectDye-sensitized solar cells
dc.subjectFlavylium salts
dc.subjectTitanium dioxide
dc.subjectGeneral Chemical Engineering
dc.subjectProcess Chemistry and Technology
dc.titleExploring the impact of structural rigidification of amino-substituted bio-inspired flavylium dyes in DSSCsen
dc.typejournal article
degois.publication.titleDyes and Pigments
degois.publication.volume218
dspace.entity.typePublication
oaire.awardNumberUIDP/50006/2020
oaire.awardNumberPD/BD/135087/2017
oaire.awardNumberUIDB/00313/2020
oaire.awardNumberUIDP/00313/2020
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleTriplet States of Flavylium Dyes in Smart Textile Photovoltaics
oaire.awardTitleCoimbra Chemistry Center
oaire.awardTitleCoimbra Chemistry Center
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/PD%2FBD%2F135087%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F00313%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F00313%2F2020/PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamOE
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
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