TD-DFT study on electron transfer mobility and intramolecular hydrogen bond of substituted indigo derivatives

Ma, Ce; Li, Hui; Yang, Yonggang; Li, Donglin; Liu, Yufang

doi:10.1016/j.cplett.2015.08.012

Cited by 9 publications

(6 citation statements)

References 42 publications

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“…Orbital plots are similar for compounds 5a and 5b : the HOMO and LUMO, i.e., the FMOs involved in the lowest energy transition predicted at 604–610 nm, are localized over the indigo moiety and have a π and π* character, respectively. This charge distribution is the same found for indigo and its derivatives in previous literature papers [ 9 , 38 , 42 , 43 ].…”

Section: Resultssupporting

confidence: 89%

Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

et al. 2020

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A new series of symmetrical organic dyes containing an indigo central core decorated with different electron donor groups have been prepared, starting from Tyrian Purple and using the Pd-catalyzed Stille-Migita coupling process. The effect of substituents on the spectroscopic properties of the dyes has been investigated theoretically and experimentally. In general, all dyes presented intense light absorption bands, both in the blue and red regions of the visible spectrum, conferring them a bright green color in solution. Using the same approach, an asymmetrically substituted D–A-π–A green dye, bearing a triarylamine electron donor and the cyanoacrylate acceptor/anchoring group, has been synthesized for the first time and fully characterized, confirming that spectroscopic and electrochemical properties are consistent with a possible application in dye-sensitized solar cells (DSSC).

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Section: Resultssupporting

confidence: 89%

Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

et al. 2020

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“…, methyl, halogen, methoxy groups. 9,12,13 Replacement of both hydrogen atoms of the N–H groups in indigo by different groups has also been described and unexpected properties were observed. 14–20 Indigo derivatives, which are not secondary amines and cannot establish intramolecular hydrogen bonds, showed photoinduced isomerizations.…”

Section: Introductionmentioning

confidence: 94%

“…The more common modication consists in the replacement of hydrogen atoms at the 4-, 5-, 6-and 7-position of the phenyl ring with other atoms, or groups of atoms, e.g., methyl, halogen, methoxy groups. 9,12,13 Replacement of both hydrogen atoms of the N-H groups in indigo by different groups has also been described and unexpected properties were observed. [14][15][16][17][18][19][20] Indigo derivatives, which are not secondary amines and cannot establish intramolecular hydrogen bonds, showed photoinduced isomerizations.…”

Section: Introductionmentioning

confidence: 96%

Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives

et al. 2021

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“…Indigo, curcumin, and alizarin are natural dyes having both hydrogen bond donor and hydrogen bond acceptor sites in their structures. Concerning the hydrogen bond donor sites, indigo has secondary amine groups that establish strong intramolecular hydrogen bonds, − while both curcumin and alizarin have hydroxyl groups that can be deprotonated according to the solvent media. Moreover, curcumin is a tautomeric compound existing in its enolic or keto form according to the solvent properties. , Therefore, unlike indigo, distinct chemical structures have to be considered for a proper description of both curcumin and alizarin in solution.…”

Section: Methodsmentioning

confidence: 99%

Screening Ionic Solvents for Enhancing the Solubility of Water-Insoluble Natural Dyes

Lepre

Sabelle

Beaumard

et al. 2021

Ind. Eng. Chem. Res.

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One strategy to promote the use of natural dyes consists of developing solvents capable of increasing their solubility. Herein, in silico predictions of activity coefficients based on the conductor-like screening model COSMO-SAC were used to screen the most promising ionic solventsionic liquids or eutectic mixturesfor the dissolution of three natural dyes, namely, indigo, alizarin, and curcumin. The predicted logarithmic activity coefficients at infinite dilution, lnγ∞, indicate that small ions having high charge density and capable of establishing strong hydrogen bonds appear to be the best candidates. Anions such as acetate, methanesulfonate, chloride, bromide, and methyl- or ethyl-sulfate combined with small tetraalkylammonium-based, pyrrolidinium-based, and imidazolium-based cations seem to be the best candidates for the interaction and thus possible dissolution of the natural dyes. The eutectic mixture of such small cation–anion combinations with primary amines, small carboxylic acids, and zwitterions such as betaine and carnitine can lead to ionic solvents that are liquids at room temperature. The chosen potential ionic solvents were prepared, and the experimental solubility of the three natural dyes was measured and compared with that in water.

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TD-DFT study on electron transfer mobility and intramolecular hydrogen bond of substituted indigo derivatives

Cited by 9 publications

References 42 publications

Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

Synthesis and Characterization of New Organic Dyes Containing the Indigo Core

Deep in blue with green chemistry: influence of solvent and chain length on the behaviour of N- and N,N′- alkyl indigo derivatives

Screening Ionic Solvents for Enhancing the Solubility of Water-Insoluble Natural Dyes

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