Optical properties of wine pigments: theoretical guidelines with new methodological perspectives

Trouillas, Patrick; Meo, Florent Di; Gierschner, Johannes; Linares, Mathieu; Sancho‐García, Juan Carlos; Otyepka, Michal

doi:10.1016/j.tet.2014.10.046

Cited by 29 publications

(58 citation statements)

References 89 publications

(72 reference statements)

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“…Unlike common anthocyanins, PA1 and PA2 do not clearly undergo such relatively fast color loss in agreement with previous investigations on various PAs [11,19]. Thus far, the sole PAs whose cationic form has been clearly shown to be electrophilic enough to add water (at C10) are the acetylpyranoanthocyanins (stemming from the addition of diacetyl-2,3-butanedione to anthocyanins) owing to the electron-withdrawing effect of the acetyl group [20]. By contrast, the visible spectra of PA1 and PA2 in the pH range 2.0–3.5 are essentially stable over time and identical to the spectra under highly acidic conditions (pH = 1), in which AH + is the sole species.…”

Section: Resultssupporting

confidence: 87%

“…Geometry optimization were achieved using density functional theory (DFT) calculations with the hybrid functional B3P86, which has appeared particularly adapted to assess both the thermodynamic and UV-visible absorption properties of polyphenols [20,25]. The Pople-type triple-ζ basis set, namely 6-31+G(d,p), allowed to establish reliable structure-property (UV-visible absorption) relationships for large series of polyphenols at a reasonable computational time [26].…”

Section: Methodsmentioning

confidence: 99%

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p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

Vallverdú‐Queralt

Biler

Meudec

et al. 2016

IJMS

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The physicochemical properties of the wine pigments catechyl-pyranomalvidin-3-O-glucoside (PA1) and guaiacyl-pyranomalvidin-3-O-glucoside (PA2) are extensively revisited using ultraviolet (UV)-visible spectroscopy, dynamic light scattering (DLS) and quantum chemistry density functional theory (DFT) calculations. In mildly acidic aqueous solution, each cationic pigment undergoes regioselective deprotonation to form a single neutral quinonoid base and water addition appears negligible. Above pH = 4, both PA1 and PA2 become prone to aggregation, which is manifested by the slow build-up of broad absorption bands at longer wavelengths (λ ≥ 600 nm), followed in the case of PA2 by precipitation. Some phenolic copigments are able to inhibit aggregation of pyranoanthocyanins (PAs), although at large copigment/PA molar ratios. Thus, chlorogenic acid can dissociate PA1 aggregates while catechin is inactive. With PA2, both chlorogenic acid and catechin are able to prevent precipitation but not self-association. Calculations confirmed that the noncovalent dimerization of PAs is stronger with the neutral base than with the cation and also stronger than π–π stacking of PAs to chlorogenic acid (copigmentation). For each type of complex, the most stable conformation could be obtained. Finally, PA1 can also bind hard metal ions such as Al3+ and Fe3+ and the corresponding chelates are less prone to self-association.

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Section: Resultssupporting

confidence: 87%

Section: Methodsmentioning

confidence: 99%

p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

Vallverdú‐Queralt

Biler

Meudec

et al. 2016

IJMS

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“…Anthocyanins are usually present in their flavylium cation form, which is mainly responsible for the absorption of the light. However, this form is only favored at low pKa which is the case in F3 (Trouillas et al, 2015). Fig.…”

Section: Resultsmentioning

confidence: 85%

Efficiency enhancement of Ixora floral dye sensitized solar cell by diminishing the pigments interactions

Thotagamuge

Petrović²,

Peiris

et al. 2015

Solar Energy

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“…The presence of anthocyanin in each dye extract was confirmed by adding a few drops of hydrochloric acid, which resulted in the formation of bright red coloration. The change in color is due to an equilibrium shift of anthocyanin toward their flavylium cation (AH + ) at low pH [35]. UV-Vis measurement was also carried out and intense peaks can be observed between 500 and 550 nm confirming the presence of anthocyanin molecules, which are known to absorb light strongly between those wavelength ranges at pH 1.0 [36].…”

Section: Resultsmentioning

confidence: 99%

Tailoring of extraction solvent of Ixora coccinea flower to enhance charge transport properties in dye-sensitized solar cells

Lim

Damit

Ekanayake

2015

Ionics

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We have tailored the extraction solvent of natural anthocyanin pigments from Ixora coccinea flower to lower charge transport resistance and enhance effective electron diffusion coefficient as well as absorption properties in DSSC sensitization. Six different extraction solvents were used in this study, namely, absolute ethanol, 70 % ethanol, acetone, dimethyl formamide, dimethyl sulfoxide, and distilled water. Dimethyl formamide was found to be able to extract the most anthocyanins from the Ixora flower, followed by dimethyl sulfoxide, acetone, absolute ethanol, 70 % ethanol, and distilled water, respectively. Dye-sensitized solar cells were fabricated using these extracted dyes as sensitizers and the cell performances were measured and characterized. The dye-sensitized solar cell equipped with a dye sensitizer extracted in 70 % ethanol achieved the highest conversion efficiency (ɳ=0.50±0.04 %) owing to its highest electron diffusion coefficient and lowest transport resistance in the TiO 2 /dye/electrolyte interface. This was followed by the cell equipped a with dye sensitizer extracted in acetone (ɳ=0.30±0.04 %), absolute ethanol (ɳ= 0.27±0.01 %), dimethyl formamide (ɳ=0.17±0.01 %), dimethyl sulfoxide (ɳ=0.16±0.01 %), and distilled water (ɳ= 0.09±0.003 %) in conversion efficiency performances, respectively. This study provides an insight into the importance of choosing the right medium for both dye extraction as well as the favorable solvent medium for dye adsorption onto TiO 2 .

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Optical properties of wine pigments: theoretical guidelines with new methodological perspectives

Cited by 29 publications

References 89 publications

p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

p-Hydroxyphenyl-pyranoanthocyanins: An Experimental and Theoretical Investigation of Their Acid—Base Properties and Molecular Interactions

Efficiency enhancement of Ixora floral dye sensitized solar cell by diminishing the pigments interactions

Tailoring of extraction solvent of Ixora coccinea flower to enhance charge transport properties in dye-sensitized solar cells

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