Syntheses and UV–visible spectroscopic properties of new ‘fluorophilic’ fluorine‐ and perfluoroalkyl‐substituted solvatochromic pyridinium N‐phenolate betaine dyes

Reichardt, Christian; Eschner, Michael; Schäfer, Gerhard

doi:10.1002/poc.427.abs

Cited by 12 publications

(19 citation statements)

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“…e determination of the dye uptake into polyester fibers was measured applying the absorption process depending on the Beer-Lambert law. is was evaluated by the testing sample from dye bath at different periods of time (15,40,55,75,90,105,120,135,150,160,170, and 180 minutes) while running the dyeing process, according to the previously reported techniques [4,7].…”

Section: Dyeingmentioning

confidence: 99%

“…Generally, a solvatochromic material can be defined as a chemical substance able to alter its color in solvents of different polarities due to a variation in its absorption or emission spectra in each solvent. ere is a variety of solvatochromic dyes that have been discovered recently, such as pyridinium, merocyanine, and stilbazolium dyes [9][10][11][12][13][14][15].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

Khattab

Allam

Othman

et al. 2019

Journal of Chemistry

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New tricyanofuran intramolecular charge transfer dyes comprising the hydrazone group were prepared and fully characterized in order to study their possible solvatochromism, dyeing ability, and antimicrobial activity. e preparation of the hydrazone dyes was achieved in relatively good yields starting from different aromatic amines. e hydrazone functional group was presented via the azo-coupling reaction of the tricyanofuran compound by the properly substituted diazonium chloride. Chemical structures of the prepared hydrazones were confirmed via nuclear magnetic resonance spectroscopy ( 1 H-and 13 C-NMR), Fourier-transform infrared spectroscopy (FT-IR), and elemental analysis (C, H, and N). e UV-visible absorption spectra of the produced sensor colorants displayed interesting solvatochromism in solvents with a different polarity, which was found to be affected by the substituents bonded to the aromatic hydrazone moiety. e pH molecular switching was investigated through tuning the intramolecular charge transfer stimulated by the reversible deprotonation/protonation process in acetonitrile solution showing color change from yellow to purple. e produced disperse dyestuffs were employed for dyeing polyester fibers to introduce acceptable color strength and colorfastness properties. Moreover, the dyes verified a weak to moderate antimicrobial activity against some selected pathogens, including S. aureus, E. coli, and Candida albicans.

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Section: Dyeingmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

Khattab

Allam

Othman

et al. 2019

Journal of Chemistry

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“…Examples are polymer and hybrid electron‐accepting materials based on semiconducting perfluorophenylquinoline (P5FQ),2 the sensitization of TiO 2 nanoparticles, electrodes with perfluoroaryl motif in organic semioconducting dyes for photochemical applications (Ph5FQ‐TiO 2 ),3 and betaine dyes for determination of solvent polarity (eicosanfluoro (F 20 )‐substituted betaine dye) (Figure 1). 4…”

Section: Methodsmentioning

confidence: 99%

A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes

Yuen

Charoensak

et al. 2015

Chemistry An Asian Journal

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The first general examples of direct coupling of heteroaryl chlorides, especially substituted 2-pyridyl chlorides which were previously found to be problematic, with electron-deficient polyfluoroarenes are reported. Pd(OAc)2 associated with 3-(dicyclohexylphosphino)-2-phenylindole L1 serves as the effective catalyst which allows the challenging direct coupling of heteroaryl chlorides and polyfluoroarenes. In addition to heterocycles, a wide range of non-activated and activated aryl chlorides and alkenyl chlorides were also applicable under this catalyst system. A catalyst loading down to 1 mol % Pd can be achieved.

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“…Reichardt's dye is a well-known solvatochromic dye and has been used to determine the polarity of solvents. [10] It exhibits a strong absorption maximum that changes in response to the solvent conditions. The shifting UV-visible absorption maximum of Reichardt's dye has been used extensively to determine the polarity of solvents.…”

Section: Introductionmentioning

confidence: 99%

Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - a potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals

Corrigan¹,

Whitcombe²,

McCrossen³

et al. 2009

j pharm pharmacol

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Syntheses and UV–visible spectroscopic properties of new ‘fluorophilic’ fluorine‐ and perfluoroalkyl‐substituted solvatochromic pyridinium N‐phenolate betaine dyes

Cited by 12 publications

References 0 publications

Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

Synthesis, Solvatochromic Performance, pH Sensing, Dyeing Ability, and Antimicrobial Activity of Novel Hydrazone Dyestuffs

A General Direct Arylation of Polyfluoroarenes with Heteroaryl and Aryl Chlorides Catalyzed by Palladium Indolylphosphine Complexes

Reichardt's dye and its reactions with the alkylating agents 4-chloro-1-butanol, ethyl methanesulfonate, 1-bromobutane and Fast Red B - a potentially useful reagent for the detection of genotoxic impurities in pharmaceuticals

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