Synthesis and structural characterization of novel pyranoluteolinidin dyes

Cruz, Luís; Sousa, Joana L. C.; Marinho, Andreia; Mateus, Nuno; Freitas, Víctor de

doi:10.1016/j.tetlet.2016.11.123

Cited by 16 publications

(14 citation statements)

References 20 publications

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“…Furthermore, pyranoanthocyanins have been shown to display higher color intensity and stability at a wider pH range comparatively to their anthocyanin precursors. 23,24 In fact, while anthocyanins practically lose their red color between pH 1 and 5, as a result of the formation of colorless hemiketals, pyranoanthocyanins practically do not change their color intensity. 23,24 For these reasons, these dyes are interesting for a wide range of potential applications namely as food colorants, hair dyes, laser dyes, as well as photosensitizers for medical applications namely in photodynamic therapy and for energy applications such as DSSCs.…”

Section: Introductionmentioning

confidence: 99%

“…23,24 In fact, while anthocyanins practically lose their red color between pH 1 and 5, as a result of the formation of colorless hemiketals, pyranoanthocyanins practically do not change their color intensity. 23,24 For these reasons, these dyes are interesting for a wide range of potential applications namely as food colorants, hair dyes, laser dyes, as well as photosensitizers for medical applications namely in photodynamic therapy and for energy applications such as DSSCs. 25,26 However, these natural occurring dyes develop through Nature's evolution process, optimizing and rearranging according to its needs.…”

Section: Introductionmentioning

confidence: 99%

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Catechol versus carboxyl linkage impact on DSSC performance of synthetic pyranoflavylium salts

et al. 2019

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Anthocyanins are the main polyphenolic dyes found in young red wines, which are transformed into more stable structures such as pyranoanthocyanins, during wine ageing and maturation. While anthocyanins practically lose their red color between pH 1 and 5, as a result of the formation of colorless hemiketals, pyranoanthocyanins practically do not change their color intensity. For that they constitute a photosensitizer family with great potential for bio-inspired dye-sensitized solar cells (DSSCs). In this work, a series of pyranoanthocyanin derivatives were designed, synthesized and applied for the first time as dye sensitizers in DSSCs. A relation was established between dye structure and cell efficiency. Specifically, the influence of different linker units, carboxyl and catechol, was studied in terms of their influence in the various parameters related to DSSC efficiency. The presence of the catechol unit was shown to be essential for efficient electron injection of the dye into the TiO 2 semiconductor, since carboxylic units showed a deleterious effect in electron injection due to their electron withdrawing character. An overall efficiency of 1.15% was obtained for the best performing compound, 10-catecholpyrano-3',4',5,7tetrahydroxyplavylium, with no further optimization.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Catechol versus carboxyl linkage impact on DSSC performance of synthetic pyranoflavylium salts

et al. 2019

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“…In addition, pyrano‐3‐deoxyanthocyanidin (Figure G), a novel derivative, was synthesized from the cycloaddition between 3‐deoxyanthocyanidin and double bond containing molecules such as acetaldehyde, pyruvic acid, carboxylic acid, and vinylcatechin (Cruz, Sousa, Marinho, Mateus, & de Freitas, ; Sousa et al., , ). Pyrano‐3‐deoxyanthocyanidin has an additional fourth pyranic ring that enhances electron delocalization of the system which makes it more stable against pH variations and bleaching by SO 2 than its homologous 3‐deoxyanthocyanidins and anthocyanins (Sousa et al., ).…”

Section: Chemical Synthesismentioning

confidence: 99%

3‐Deoxyanthocyanidin Colorant: Nature, Health, Synthesis, and Food Applications

Xiong

Zhang

Warner

et al. 2019

Comp Rev Food Sci Food Safe

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3‐Deoxyanthocyanidins are a rare type of anthocyanins that are present in mosses, ferns, and some flowering plants. They are water‐soluble pigments and impart orange‐red and blue‐violet color to plants and play a role as phytoalexins against microbial infection and environmental stress. In contrast to anthocyanins, the lack of a hydroxyl group at the C‐3 position confers unique chemical and biochemical properties. They are potent natural antioxidants with a number of potential health benefits including cancer prevention. 3‐Deoxyanthocyanidin pigments have attracted much attention in the food industry as natural food colorants, mainly due to their higher stability during processing and handling conditions compared with anthocyanins. They are also photochromic compounds capable of causing a change in “perceived” color, when exposed to UV light, which can be used to design novel foods and beverages. Due to their interesting properties and potential industrial applications, great efforts have been made to synthesize these compounds. For biosynthesis, researchers have discovered the 3‐deoxyanthocyanidin biosynthetic pathway and their biosynthetic genes. For chemical synthesis, advances have been made to synthesize the compounds in a simpler and more efficient way as well as looking for its novel derivative with enhanced coloration properties. This review summarizes the developments in the research on 3‐deoxyanthocyanidin as a colorant, from natural sources to chemical syntheses and from health benefits to applications and future prospects, providing comprehensive insights into this group of interesting compounds.

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“…In the last decade, the efforts of our research group have been dedicated to the synthesis, isolation, and characterization of natural and bioinspired pyranoflavylium-type dyes. [5][6][7][8][9][10] These pigments have much greater color stability over a wide pH range than their precursors, because the C-4 position of the C ring is blocked by the additional pyran ring. This prevents the hydration reaction and, thereby, the appearance of a colorless hemiketal form.…”

Section: Syn Lettmentioning

confidence: 99%

Bioinspired Synthesis and Physical-Chemical Properties of a New 10-Methylpyrano-4′-hydroxyflavylium Chloride Salt

Gomes¹,

Guimarães²,

Gonçalves³

et al. 2019

Synlett

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A novel bioinspired 10-methylpyranoflavylium dye was synthesized. The dye was fully characterized by LC-DAD/ESI-MS and NMR 1D and 2D techniques, and its equilibrium constants towards pH variations were determined by UV–vis titration. These studies revealed the presence of three species (a flavylium cation AH+, a neutral quinoidal base A, and an anionic quinoidal base A–) in the pH range 1–12, driven by the two pK a values of the dye: pK a1 = 6.8 ± 0.1 and pK a2 = 10.8 ± 0.1. The first deprotonation of the dye occurs within the pH range for spoilage of many packed-food products, making the dye an excellent candidate for use as a pH sensor for real-time monitoring of the quality and freshness of foods.

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Synthesis and structural characterization of novel pyranoluteolinidin dyes

Cited by 16 publications

References 20 publications

Catechol versus carboxyl linkage impact on DSSC performance of synthetic pyranoflavylium salts

Catechol versus carboxyl linkage impact on DSSC performance of synthetic pyranoflavylium salts

3‐Deoxyanthocyanidin Colorant: Nature, Health, Synthesis, and Food Applications

Bioinspired Synthesis and Physical-Chemical Properties of a New 10-Methylpyrano-4′-hydroxyflavylium Chloride Salt

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