Electron Spin Resonance Spectra of the Basic Indigoid Dye Radicals

Bruin, F.; Heineken, F. W.; Bruin, M.

doi:10.1021/jo01037a501

Cited by 27 publications

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“…The latter form has been studied spectroscopically and computationally in connection with its reported occurrence in Maya Blue pigments . As an intermediate in the stepwise oxidation of Ind 2– , a radical-state Ind •– (eq ) can be formulated …”

Section: Introductionmentioning

confidence: 99%

Noninnocence of Indigo: Dehydroindigo Anions as Bridging Electron-Donor Ligands in Diruthenium Complexes

et al. 2016

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Complexes of singly or doubly deprotonated indigo (H2Ind) with one or two [Ru(pap)2](2+) fragments (pap = 2-phenylazopyridine) have been characterized experimentally [molecular structure, voltammetry, electron paramagnetic resonance (EPR), and UV-vis-near-IR spectroelectrochemistry] and by time-dependent density functional theory calculations. The compound [Ru(pap)2(HInd(-))]ClO4 ([1]ClO4) was found to contain an intramolecular NH---O hydrogen bond, whereas [{Ru(pap)2}2(μ-Ind(2-))](ClO4)2 ([2](ClO4)2), isolated as the meso diastereoisomer with near-IR absorptions at 1162 and 991 nm, contains two metals bridged at 6.354 Å distance by the bischelating indigo dianion. The spectroelectrochemical study of multiple reversible reduction and oxidation processes of 2(n) (n = 4+, 3+, 2+, 1+, 0, 1-, 2-, 3-, 4-) reveals the stepwise addition of electrons to the terminal π-accepting pap ligands, whereas the oxidations occur predominantly at the anionic indigo ligand, producing an EPR-identified indigo radical intermediate and revealing the suitability of deprotonated indigo as a σ- and π-donating bischelating bridge.

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Section: Introductionmentioning

confidence: 99%

Noninnocence of Indigo: Dehydroindigo Anions as Bridging Electron-Donor Ligands in Diruthenium Complexes

et al. 2016

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“…In response to volatiles emitted from herbivore-infested plants (HIPVs), neighboring intact plants enhance either their direct defense (i.e., becoming a less suitable resource for herbivores [155][156][157][158] ) or their indirect defense (i.e., attracting carnivorous natural enemies of herbivores [159][160][161][162] ). Such responses of plants prior to biotic stress are called priming.…”

Section: 08132(iii) Hipvs Affect Neighboring Plant's Indirect Dementioning

confidence: 99%

Chemical Defence and Toxins of Plants

Yamane

Konno

Sabelis

et al. 2010

Comprehensive Natural Products II

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“…An interesting linking of the ancient and the modern was the demonstration of the identity of "Tyrian Purple" and 6,6'-dibromoindigo. Bruin, Heineken, and Bruin (47) followed directions of Pliny and Aristotle to prepare samples from the same species of mollusks as those whose shells are found in the ancient Mediterranean heaps where the dye was prepared. The ESR spectrum wras then compared with that of authentic 6,6'-dibromoindigo and found to be identical.…”

Section: Electron Spin Resonancementioning

confidence: 99%

Magnetic Resonance Spectrometry

Foster¹

1964

Anal. Chem.

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Electron Spin Resonance Spectra of the Basic Indigoid Dye Radicals

Cited by 27 publications

References 0 publications

Noninnocence of Indigo: Dehydroindigo Anions as Bridging Electron-Donor Ligands in Diruthenium Complexes

Noninnocence of Indigo: Dehydroindigo Anions as Bridging Electron-Donor Ligands in Diruthenium Complexes

Chemical Defence and Toxins of Plants

Magnetic Resonance Spectrometry

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