Indoaniline Dyes Research Articles

Optical macromolecular indoaniline indicators for vinyl‐SiH curing of silicones for dental application

AbstractIn this paper we present a poly siloxane containing covalently bound indoaniline dye, which decolorizes during reaction with a poly siloxane bearing vinyl and Si‐H groups in the presence of a Karstedt catalyst. Poly siloxane bearing indoaniline endgroups were prepared from (2‐allyl‐4‐(4‐(ethyl(2‐hydroxyethyl)amino)phenylimino)‐ 6‐methoxycyclohexa‐2,5‐dienone respectively 2‐allyl‐4‐(4‐(ethyl(2‐hydroxyethyl)amino)phenylimino)cyclohexa‐2,5‐ dienone) and Si‐H terminated poly siloxane. The structure was verified by IR‐, 1H‐NMR spectroscopy, and MALDI‐TOF mass spectrometry. The obtained blue colored poly siloxane is suitable as dye indicator for crosslinking, for example, for a time‐controlled preparation of dental impressions. Copyright © 2009 John Wiley & Sons, Ltd.

Ab initio Study of Ultrafast Photochemical Reaction Dynamics of Phenol Blue

Phenol blue (PB) is a primary skeletal structure part of indoaniline dyes and well-known as a solvatochromic dye. It has been recently observed by pump-probe (PP) transient absorption measurements that PB shows ultrafast ground state recovery within a few hundred femtoseconds after photoexcitation. In this work, the ultrafast photochemical reaction mechanism of PB has been investigated using direct ab initio (CASSCF) nonadiabatic molecular dynamics with the trajectory surface hopping (TSH) method. The swarm of trajectories starting from the S1 Franck-Condon (FC) point has mostly shown surface hops (nonadiabatic transitions) from the S1 state to the S0 state at 110-120 fs in the vicinity of an S1/S0 conical intersection and after decay to the S0 state bifurcated into two (Reverse and Forward) directions with almost the same branching ratio and reached the vicinity of the S0 minimum energy point at 200-300 fs, which is in good agreement with the fast time component of the ground state recovery in the PP measurements. After reaching the vicinity of the S0 minimum energy point, the trajectories showed a coherent vibration of bending motion between quinoneimine and aniline rings with a low frequency of 43 cm-1, which presumably corresponds to a coherently photoexcitation-induced vibrational mode with a low frequency recently observed by the PP measurements.

Effect of metal ions on the absorption spectra and surface plasmon resonance of an azacrown indoaniline dye

The effects of the complexation of a metal ion with an azacrown indoaniline ( ACIA) dye on absorption spectra were evaluated using the Pariser–Parr–Pople (PPP-MO) method. The ACIA dye carrying a monoazacrown moiety exhibited sensitivity to metal ion complexation using an optical sensor based on surface plasmon resonance (SPR). A multilayer sensing chip was prepared with the ACIA dye sensing layer coated on a gold layer. Using the ACIA dye as a metal ion sensing molecule, a highly selective response to Li + was observed.

Azacrown indoaniline dye as a sensing molecule in optical sensors for the selective detection of Li +

The complex formation of azacrown indoaniline ( ACIA) dye 9 with Li + and Na + was investigated spectrophotometrically. As the polarity of the solvent decreased, the complexation ability increased. ACIA 9 exhibits higher Li + selectivity than Na + ion in CH 2Cl 2–CH 3CN. The specific spectral response to Li + ion by ACIA 9 indicates potential suitability for optical sensor applications.

Synthesis and X-ray structural characterization of indoaniline dye carrying a monoazacrown moiety

An indoaniline dye carrying a monoazacrown moiety was prepared by condensation of 10-(4′-nitrosophenyl)-1,4,7-trioxa-10-azacyclododecane with α-nahpthol. The crystal structure was determined by X-ray crystallography and the crystal was found to exist in the monoclinic space group P2 1/c (No. 14). Results showed that this dye is non-planar, with a dihedral angle of 36.53° between the quinonimine and aniline moieties. In the crystal, two different streoisomers are stacked alternately.

Relationship between π-Conjugation Size and Electronic Absorption Spectrum: Novel π-Conjugation Size Dependence of Indoaniline Dyes

When the π-system at the quinone moiety in indoaniline dyes is expanded, the maximum absorption wavelength (λmax) of the main band in the absorption spectrum shows a shift to shorter wavelength (hypsochromic shift). This behavior stands in contrast to the generally accepted rule that expansion of a π-system leads to a bathochromic shift in the absorption spectrum, and the behavior was therefore investigated using the INDO/S method. It could be shown that the present systems are multicomponent systems, in which highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) are located on different parts of the molecule. Therefore, only the LUMO rises in energy when the quinone system expands, thus leading to a widening of the HOMO−LUMO energy gap.

Synthesis of 4-Aminophenyl N-Acetyl-.BETA.-D-glucosaminide Derivatives and Their Application to the Rate-Assay of N-Acetyl-.BETA.-D-glucosaminidase.

Four N-acetyl-β-D-glucosaminides, 4-amino-2, 6-dibromophenyl (1a), 4-amino-2, 6-dichlorophenyl (1b), 4-amino-2-chlorophenyl (1c) and 4-aminophenyl N-acetyl-β-D-glucosaminides (1d) were synthesized. Substrates 1a-c were hydrolyzed by N-acetyl-β-D-glucosaminidase and the released aglycones reacted with N-ethyl-N-(3-methylphenyl)-N'-succinylethylenediamine to produce indoaniline dyes in the presence of bilirubin oxidase under weakly acidic rate-assay conditions (pH 5.0). The Km values for 1a-c were 1.97, 1.65 and 1.39 mM, respectively. Among these compounds, 1b is considered to be the substrate with most potential for the rate-assay of N-acetyl-β-D-glucosaminidase, since it showed the largest Vmax value and the strongest color generation from colorless to green (λmax 302→718 nm)following enzyme hydrolysis and the coupling reaction. Furthermore, 1b was moderately soluble and stable in aqueous solution and exhibited about a 5.9-fold higher sensitivity to the enzyme than 2-chloro-4-nitrophenyl N-acetyl-β-D-glucosaminide.

The relationship between the structures and absorption spectra of cyan color indoaniline dyes

The absorption spectra of 23 indoaniline dyes were calculated on the AM1-optimized structures by means of the INDO/S method. The observed and calculated absorption wavelengths showed good correlation for the main (longest wavelength) absorption bands (observed at 560-670 nm), and there was fair correlation between the observed molar extinction coefficients and the calculated oscillator strengths. The observed absorption wavelengths could be reproduced by the calculation for the subabsorption bands near the visible region (observed at 320-380 nm)

Theoretical and experimental studies of indoaniline dyes. A novel relationship between absorption spectra and molecular structure

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTTheoretical and experimental studies of indoaniline dyes. A novel relationship between absorption spectra and molecular structureMasafumi Adachi, Yukichi Murata, and Shinichiro NakamuraCite this: J. Am. Chem. Soc. 1993, 115, 10, 4331–4338Publication Date (Print):May 1, 1993Publication History Published online1 May 2002Published inissue 1 May 1993https://doi.org/10.1021/ja00063a059RIGHTS & PERMISSIONSArticle Views242Altmetric-Citations29LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (799 KB) Get e-Alerts Get e-Alerts

Dark stability of dye transfer sheet with indoaniline dyes

Dark stability of dye transfer sheet with indoaniline dyes

Molecular structure and electronic spectrum of organic colorants. (2). Molecular orbital approach to indoaniline dyes.

Molecular structure and electronic spectrum of organic colorants. (2). Molecular orbital approach to indoaniline dyes.

New chromoionophores based on indoaniline dyes containing calix[4]arene

A new set of chromoionophores having indoaniline and calix[4]arene segments have been prepared, the ethylacetate derivative of which shows a high selectivity for Na +. Sodium ion binding induces a bathochromic shift in the absorption spectrum of this chromoionophore leading to the suggestion that this class of compounds could have potential use as an optical sensor for Na + detection.

Molecular structure and electronic spectrum of organic colorants: Molecular orbital approach to indoaniline dyes.

The applicability of semi-empirical PPP and INDO/S molecular orbital calculations For indoanilines (3) was investigated under three structural points of view: syn/anti isomerization, resonance canonical structures, and non-planarity of the molecule.

Determination of salbutamol in human plasma and urine by high-performance thin-layer chromatography

A rapid, accurate and sensitive method for the determination of salbutamol in plasma and urine is described. Salbutamol is extracted using solid-phase techniques and converted to an indoaniline dye by reaction with dimethyl- p-phenylenediamine. The indoaniline is separated using high-performance thin-layer chromatography and quantified by absorption microdensitometry at 650 nm. The method is sensitive down to 20 ng/ml in urine and to 1 ng/ml in plasma and provides data in good agreement with that obtained by gas chromatography—mass spectrometry. The method can be used for analysis of pharmacokinetic studies.

Photoreduction of azomethine and indoaniline dyes sensitized by benzophenone

1. The highly efficient photodecomposition of azomethine and indoaniline dyes occurs in the presence of benzophenone as a result of their reduction of ketyl radicals formed in the system. 2. The intermediate in the reduction of these dyes, AH radical, participates in the acid-base equilibrium and loses a proton in alkaline media.

Benzoquinone imines. Part VII. The mechanism and kinetics of the reaction of p-benzoquinone di-imines with monohydric phenols and the ultraviolet, infrared, and nuclear magnetic resonance spectra of the resulting indoanilines

The reaction of p-benzoquinone di-imine and its C-methyl and C-chloro-derivatives with monohydric phenols is shown to give indoaniline dyes, by a two-step reaction involving a rate-controlling electrophilic attack of the conjugate acid of the di-imine on both the phenoxide ion and the neutral phenol. The resulting 4-amino-4′-hydroxy-diphenylamine then suffers rapid oxidation by a second molecule of di-imine to give the indoaniline dye. The reactivity of the phenoxide ion is increased by methylation and decreased by chlorination. At a fixed pH the rate of reaction of the di-imine with a particular phenoxide ion is decreased by C-methylation of the di-imine and increased by C-chlorination. These substituent effects have been found to be additive. The u.v., i.r., and n.m.r. spectra of the C-methylated indoaniline dyes are tabulated and shown to indicate that the dyes exist as the N-(4-aminophenyl)-p-benzoquinone monoimines rather than as the N-(4-hydroxyphenyl)-p-benzoquinone di-imines.

The Effect of Solubilization by Surfactants on the Kinetics of Alkaline Decomposition of Indoaniline Dyes

The Effect of Solubilization by Surfactants on the Kinetics of Alkaline Decomposition of Indoaniline Dyes

Indoaniline Dyes. V.1 Some Dyes Derived from Substituted α-Naphthols

Indoaniline Dyes. V.¹ Some Dyes Derived from Substituted α-Naphthols

Indoaniline Dyes. III. Coupling of para-Substituted Phenols with Oxidized p-Aminodimethylaniline

Indoaniline Dyes. III. Coupling of para-Substituted Phenols with Oxidized <i>p</i>-Aminodimethylaniline

Indoaniline Dyes. I. Some Phenol Blue Derivatives with Substituents in the Phenol Ring

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTIndoaniline Dyes. I. Some Phenol Blue Derivatives with Substituents in the Phenol RingPaul W. Vittum and Gordon H. BrownCite this: J. Am. Chem. Soc. 1946, 68, 11, 2235–2239Publication Date (Print):November 1, 1946Publication History Published online1 May 2002Published inissue 1 November 1946https://doi.org/10.1021/ja01215a035RIGHTS & PERMISSIONSArticle Views214Altmetric-Citations34LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (493 KB) Get e-Alerts Get e-Alerts