Highly fluorescent hybrid pigments from anthocyanin- and red wine pyroanthocyanin-analogs adsorbed on sepiolite clay

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dc.contributor.authorSilva, Gustavo Thalmer M.
dc.contributor.authorda Silva, Karen M.
dc.contributor.authorSilva, Cassio P.
dc.contributor.authorRodrigues, Ana Clara B.
dc.contributor.authorOake, Jessy
dc.contributor.authorGehlin, Marcelo H.
dc.contributor.authorBohne, Cornelia
dc.contributor.authorQuina, Frank H.
dc.date.accessioned2020-07-22T20:06:10Z
dc.date.available2020-07-22T20:06:10Z
dc.date.copyright2019en_US
dc.date.issued2019
dc.description.abstractFlavylium cations serve as models for the chemical and photochemical reactivity of anthocyanins, the natural plant pigment responsible for many of the red, blue and purple colors of fruits and flowers. Likewise, pyranoflavylium cations serve as models of the fundamental chromophoric moiety of pyranoanthocyanins, molecules that can form from reactions of grape anthocyanins in red wines during their maturation. In the present work, hybrid pigments are prepared by the adsorption of a series of five synthetic flavylium cations (FL) and five synthetic pyranoflavylium cations (PFL) on sepiolite clay (SEP). The FL are smaller in size than the PFL, but both can in principle fit into the tunnels and/or external grooves (with dimensions of 3.7 × 10.6 Å) of SEP. Measurements of the fluorescence quantum yields of the adsorbed dyes indicate that they are at least as fluorescent as in acidic acetonitrile solution, and in a few cases substantially more fluorescent. The observation of biexponential fluorescence decays is consistent with emission from dye molecules adsorbed at two distinct sites, presumably tunnels and grooves. These hybrid materials also have improved properties in terms of stability of the color in contact with pH 10 aqueous solution and resistance to thermal degradation of the dye. SEP thus appears to be a promising substrate for the development of highly fluorescent flavylium or pyranoflavylium cation-derived hybrid pigments with improved color and thermal stability.en_US
dc.description.reviewstatusRevieweden_US
dc.description.scholarlevelFacultyen_US
dc.description.sponsorshipThis study was financed in part by the Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - Brasil (CAPES) - Finance Code 001. The authors also thank the CNPq (F. H. Q. Universal grant 408181/2016-3), INCT-Catálise (CNPq 465454/2014-3), and NAP-PhotoTech for the support, the CNPq for a research productivity fellowships (F. H. Q. and M. H. G.) and undergraduate fellowship (K. M. S.), and CAPES for graduate fellowships (G. T. M. S. and C. P. S.). Researchers at UVic thanks NSERC (RGPIN-2017-04458) for funding and CAMTEC for the use of shared facilities. A. C. B. R. thanks the project no. 22124-LLPT-Laserlab-Portugal (ref: CENTRO-01-0145-FEDER-000014) for a post-doctoral grant.en_US
dc.identifier.citationSilva, G. T. M., da Silva, K. M., Silva, C. P., Rodrigues, A. C. B., Oake, J., Gehlen, M. H., Bohne, C., & Quina F. H. (2019). Highly fluorescent hybrid pigments from anthocyanin- and red wine pyroanthocyanin-analogs adsorbed on sepiolite clay. Photochemical & Photobiological Sciences, 18, 1750-1760. https://doi.org/10.1039/C9PP00141G.en_US
dc.identifier.urihttps://doi.org/10.1039/C9PP00141G
dc.identifier.urihttp://hdl.handle.net/1828/11951
dc.language.isoenen_US
dc.publisherPhotochemical & Photobiological Sciencesen_US
dc.subjectCentre for Advanced Materials and Related Technology (CAMTEC)
dc.subject.departmentDepartment of Chemistry
dc.titleHighly fluorescent hybrid pigments from anthocyanin- and red wine pyroanthocyanin-analogs adsorbed on sepiolite clayen_US
dc.typePostprinten_US

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