Anthraquinonoid Vat Dyes

Венкатараман, К.; Iyer, V.N.

doi:10.1016/b978-0-12-717005-3.50010-3

Cited by 13 publications

(8 citation statements)

References 114 publications

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“…Similarly, ortho -quinones formed in the oxidation of urushiol cause the contact-dermatitis associated with plants like poison ivy . Benzoquinones are also utilized in various chemical applications, serving as dyestuffs, − battery electrodes, − and hydrogen storage materials and as oxidizing agents − and dienophiles in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Photoelectron Spectroscopy Study of Quinonimides

et al. 2017

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Structures and energetics of o-, m-, and p-quinonimide anions (OCHN) and quinoniminyl radicals have been investigated by using negative ion photoelectron spectroscopy. Modeling of the photoelectron spectrum of the ortho isomer shows that the ground state of the anion is a triplet, while the quinoniminyl radical has a doublet ground state with a doublet-quartet splitting of 35.5 kcal/mol. The para radical has doublet ground state, but a band for a quartet state is missing from the photoelectron spectrum indicating that the anion has a singlet ground state, in contrast to previously reported calculations. The theoretical modeling is revisited here, and it is shown that accurate predictions for the electronic structure of the para-quinonimide anion require both an accurate account of electron correlation and a sufficiently diffuse basis set. Electron affinities of o- and p-quinoniminyl radicals are measured to be 1.715 ± 0.010 and 1.675 ± 0.010 eV, respectively. The photoelectron spectrum of the m-quinonimide anion shows that the ion undergoes several different rearrangements, including a rearrangement to the energetically favorable para isomer. Such rearrangements preclude a meaningful analysis of the experimental spectrum.

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Section: Introductionmentioning

confidence: 99%

Photoelectron Spectroscopy Study of Quinonimides

et al. 2017

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“…The x^0 values of secondary solvents were calculated by using the reciprocal eq 11 and averaging the values obtained from the six indicator solutes.…”

Section: Resultsmentioning

confidence: 99%

Solvatochromic studies of novel azo merocyanine dyes. The .pi.*azo scale of solvent polarity

Buncel¹,

Rajagopal²

1989

J. Org. Chem.

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“…The high fastness levels have been attributed to the possible presence of zwitterionic forms and hydrogen bonding. 52 Indanthren Grey M CI Vat Black X 70 Similarly, six-membered heterocycles such as acridones, quinoneazines, pyrazines, and pyrimidines are frequently incorporated into such molecules. 44 The best known of the anthraquinone vat dyes are indanthrone (61) and flavanthrone (72).…”

Section: Vat Dyesmentioning

confidence: 99%

“…33 Detailed accounts of the chemistry of viol anthrone and its derivatives have been published. 52 A related group of dyes has been derived from perylene-3,4,9,10-tetracarboxylic acid and naphthalene-l,4,5,8-tetracarboxylic acid. For example, condensation of the former with two molar equivalents of a primary aromatic or an aliphatic amine in aqueous pyridine 57 No account of vat dye chemistry would be complete without a mention of indigo (60) whose structure was elucidated by Baeyer in 1883.…”

Section: Vat Dyesmentioning

confidence: 99%

“…Farbenindustrie, the basic structure is typically synthesized by condensation of two molecules of an aromatic amine with chloranil to produce a dianilide intermediate which is converted into the triphenodioxazine dye by oxidative cyclization, occasionally in sulfuric acid in order to effect simultaneous sulfonation. Sirius Light Blue FFRL (52) was prepared by condensation of two molecules of 3-amino-N-ethylcarbazole with one molecule of chloranil and cyclization using benzene sulfonyl chloride, followed by sulfonation. Other commercially important dyes such as CI Direct Blue 109 (53), prepared from 1-aminopyrene, and CI Direct Blue 106 (54), obtained from 4-aminodiphenylaminesulfonic acid, were …”

Section: Triphenodioxazine Dyesmentioning

confidence: 99%

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