Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

Franchi, Daniele; Calamante, Massimo; Coppola, Carmen; Mordini, Alessandro; Reginato, Gianna; Sinicropi, Adalgisa; Zani, Lorenzo

doi:10.3390/molecules25153377

Cited by 11 publications

(10 citation statements)

References 63 publications

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“…They also have a large color tunability thanks to the possibility of functionalization of the parent skeleton with auxochrome groups. Consequently, a large color palette can be obtained from these dyes, thus further increasing their industrial appeal [3,4].…”

Section: Introductionmentioning

confidence: 99%

Protocols for the in-silico screening of the perceived color of industrial dyes: Anthraquinones and indigos as study cases

Tirri

Turelli

Boissonnat³

et al. 2023

Dyes and Pigments

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Section: Introductionmentioning

confidence: 99%

Protocols for the in-silico screening of the perceived color of industrial dyes: Anthraquinones and indigos as study cases

Tirri

Turelli

Boissonnat³

et al. 2023

Dyes and Pigments

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“…Indigo is a natural dye prepared from Indigofera tinctoria and Isatis tintoria plants. Due to a scarcity of natural blue dyes, indigo has played a key part in the economics of many countries since its inception, mostly for textile dyeing and printing, and it is still utilized in the fabric business today 3 . Chemical oxidation 4 , adsorption 5 , biodegradation 6 , and photolysis 7 are some of the current technologies utilized to treat wastewater.…”

Section: Introductionmentioning

confidence: 99%

Degradation of Indigo Dye Using Quantum Mechanical Calculations

Mohammed¹,

Kamil

Abduljalil

et al. 2023

Baghdad Sci.J

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The semiempirical (PM3) and DFT quantum mechanical methods were used to investigate the theoretical degradation of Indigo dye. The chemical reactivity of the Indigo dye was evaluated by comparing the potential energy stability of the mean bonds. Seven transition states were suggested and studied to estimate the actually starting step of the degradation reaction. The bond length and bond angle calculations indicate that the best active site in the Indigo dye molecule is at C10=C11. The most possible transition states are examined for all suggested paths of Indigo dye degradation predicated on zero-point energy and imaginary frequency. The first starting step of the reaction mechanism is proposed. The change in enthalpy, Gibbs free energy and change in entropy of the overall reaction are equal to -548268.223 kcal/mol, 30831.951 kcal/mol and 48.552 cal/mol.deg, respectively. The activation energy is 46176.405 kcal/mol. The reaction rate is equal to .

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“…In DSSCs, the dye is typically an organic, molecular compound, or a coordination complex, which is responsible for light harvesting and electron transfer into the conduction band (CB) of a semiconductor electrode (typically TiO 2 ) to which it is chemically bonded. Organic dyes offer high molar extinction coefficients, important for light harvesting, and an extended structural variety that can be tuned to optimize the spectral absorption range. − Despite the appealing properties of the organic sensitizers, it is mostly coordination complexes that have offered record performances in DSSCs . The first, and perhaps the most famous, class of metal complexes employed as dyes consists of ruthenium(II) polypyridyl complexes .…”

Section: Introductionmentioning

confidence: 99%

Effect of the Ancillary Ligand on the Performance of Heteroleptic Cu(I) Diimine Complexes as Dyes in Dye-Sensitized Solar Cells

Franchi

Leandri

Pizzichetti

et al. 2022

ACS Appl. Energy Mater.

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A series of heteroleptic Cu(I) diimine complexes with different ancillary ligands and 6,6′-dimethyl-2,2′-bipyridine-4,4′-dibenzoic acid (dbda) as the anchoring ligand were self-assembled on TiO 2 surfaces and used as dyes for dye-sensitized solar cells (DSSCs). The binding to the TiO 2 surface was studied by hard X-ray photoelectron spectroscopy for a bromine-containing complex, confirming the complex formation. The performance of all complexes was assessed and rationalized on the basis of their respective ancillary ligand. The DSSC photocurrent–voltage characteristics, incident photon-to-current conversion efficiency (IPCE) spectra, and calculated lowest unoccupied molecular orbital (LUMO) distributions collectively show a push–pull structural dye design, in which the ancillary ligand exhibits an electron-donating effect that can lead to improved solar cell performance. By analyzing the optical properties of the dyes and their solar cell performance, we can conclude that the presence of ancillary ligands with bulky substituents protects the Cu(I) metal center from solvent coordination constituting a critical factor in the design of efficient Cu(I)-based dyes. Moreover, we have identified some components in the I – /I 3 – -based electrolyte that causes dissociation of the ancillary ligand, i.e., TiO 2 photoelectrode bleaching. Finally, the detailed studies on one of the dyes revealed an electrolyte–dye interaction, leading to a dramatic change of the dye properties when adsorbed on the TiO 2 surface.

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Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

Cited by 11 publications

References 63 publications

Protocols for the in-silico screening of the perceived color of industrial dyes: Anthraquinones and indigos as study cases

Protocols for the in-silico screening of the perceived color of industrial dyes: Anthraquinones and indigos as study cases

Degradation of Indigo Dye Using Quantum Mechanical Calculations

Effect of the Ancillary Ligand on the Performance of Heteroleptic Cu(I) Diimine Complexes as Dyes in Dye-Sensitized Solar Cells

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