Chromogenic anionic chemosensors based on protonated merocyanine solvatochromic dyes in trichloromethane and in trichloromethane–water biphasic system

Zimmermann-Dimer, Lizandra Maria; Reis, Dalci C.; Machado, Clodoaldo; Machado, Vanderlei G.

doi:10.1016/j.tet.2009.03.049

Cited by 32 publications

(24 citation statements)

References 116 publications

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“…In the presence of an excess of the anion, the compound is deprotonated with the formation of a [HA 2 ] -complex. 12,13 This is corroborated by the fact that the experimental data used to obtain the titration curve could not be fitted using equation 1, but only with equation 2, which considers both 1:1 and 1:2 2a:anion stoichiometries.…”

Section: Resultsmentioning

confidence: 98%

“…A plot of the absorbance values at 547.0 nm as a function of c(CN -) (Figure 3b) shows a behavior typical of a 1:1 2a:CN -stoichiometry. The experimental data were fitted with the use of equation 1,[12][13][14]40,41 where Abs is the absorbance value after each addition of the anion, Abs 0 is the initial absorbance without anion added, Abs 11 is the maximum absorbance value obtained by addition of the anion considering 1:1 2a:anion stoichiometry, c(A -) is the anion concentration in each addition, and K 11 is the binding constant.…”

Section: Resultsmentioning

confidence: 99%

“…14 Recently, Reichardt's pyridiniophenolate and Brooker's merocyanine, compounds with the pyridinium cation as an acceptor center in their molecular structure, were studied in their protonated form as anionic chemosensors in acetonitrile and in trichloromethane. 12,13 Titrations with basic anions led to a 1:3 chemosensor:anion stoichiometry, which was attributed to the formation of a complex between the pyridinium group and the anion, of an electrostatic nature, prior to the interaction of the anion with the phenol moiety in the compound. 12,13 Since the pyridinium group is absent from the molecular structure of 1a and 2a, these results represent important evidence to support the model suggested for the interaction of anionic species with protonated merocyanines.…”

Section: Resultsmentioning

confidence: 99%

“…Phenol groups are commonly used in the molecular structure of these types of chemosensors. [10][11][12][13][14] The connection of the phenol donor group to an acceptor group through a conjugated bridge creates an interesting feature since the deprotonation of the compound generates a colored conjugated base. The acidity of the chemosensor can be improved by combining the effect of the medium polarity with modifications in the molecular structure of the compound.…”

Section: Introductionmentioning

confidence: 99%

“…The acidity of the chemosensor can be improved by combining the effect of the medium polarity with modifications in the molecular structure of the compound. 12,13 A set of protonated dyes with phenol donor groups in their molecular structures has been studied by our group as simple anionic chromogenic chemosensors based on acid-base strategy. [11][12][13][14] One of these dyes is 4-(4-nitrobenzylideneamine)-2,6-diphenylphenol, compound 1a, which was recently used to selectively detect CN -in the presence of several anionic species in acetonitrile with very small amounts of water.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Nicoleti

Marini

Zimmermann

et al. 2012

J. Braz. Chem. Soc.

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4-(4-Nitrobenzylideneamine)phenol was used in two strategies allowing the highly selective detection of F -and CN -. Firstly, the compound in acetonitrile acts as a chromogenic chemosensor based on the idea that more basic anions cause its deprotonation (colorless solution), generating a colored solution containing phenolate. The discrimination of CN -over F -was obtained by adding 1.4% water to acetonitrile: water preferentially solvates F -, leaving the CN -free to deprotonate the compound. Another strategy involved an assay comprised of the competition between phenolate dye and the analyte for calix [4]pyrrole in acetonitrile, a receptor highly selective for F -. Phenolate and calix[4]pyrrole form a hydrogen-bonded complex, which changes the color of the medium. On the addition of various anions, only F -was able to restore the original color corresponding to phenolate in solution due to the fact that the anion dislodges phenolate from the complexation site.

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Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Nicoleti

Marini

Zimmermann

et al. 2012

J. Braz. Chem. Soc.

View full text Add to dashboard Cite

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Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Nordhaus

Krongauz

Hai

2016

J of Applied Polymer Sci

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Solvatochromic merocyanine dyes were immobilized onto polymer surfaces and copolymerized with acrylic resins, yielding novel reversibly solvatochromic polymers, which were used as solvent polarity indicators that exhibited different colors in water and alcohols. To generate solvatochromic polymer for solvent polarity indication, two solvatochromic merocyanine dyes containing moieties, which allow their immobilization onto polymer surfaces, or copolymerization with acrylic and vinyl monomers, were sequentially synthesized in four and six steps. Merocyanine dye (E)‐2‐(2‐(1‐(6‐aminohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AHPVD) was prepared with a terminal aminohexyl group which allowed covalent bonding to activated carboxylated or sulfonated polymeric materials. The dyes were covalently bonded to the polymer surfaces, such as, nylon, polycarbonate, polyethylene terephthalate, and silicone. Solvatochromic merocyanine dye (E)‐2‐(2‐(1‐(6‐acrylamidohexyl)pyridinium‐4‐yl)vinyl)‐4,6‐dichlorophenolate (AAPVD) was synthesized for radical copolymerization with acrylate and vinyl monomers and oligomers. Side‐chain solvatochromic merocyanine‐containing hydrophilic polymers with differential water and alcohol absorption were obtained upon photoinitiated radical copolymerization with specially formulated acrylated resins. © 2016 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2017, 134, 44451.

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Synthesis of 1,8–Naphthyridines and Their Application in the Development of Anionic Fluorogenic Chemosensors

et al. 2012

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Two 1,8-naphthyridines were synthesized and found to be fluorescent in solution. These compounds were studied in the presence of Cu(+) and Cu(2+) ions and it was verified that the metal causes the quenching of their fluorescence emission, due to the formation of complexes between the naphthyridine and the metal. A displacement assay was carried out in a DMSO-water mixture with the addition of various anions to the solutions of the complexes, and it was observed that these systems have a high capacity to selectively detect cyanide.

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Chromogenic anionic chemosensors based on protonated merocyanine solvatochromic dyes in trichloromethane and in trichloromethane–water biphasic system

Cited by 32 publications

References 116 publications

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Anionic chromogenic chemosensors highly selective for fluoride or cyanide based on 4-(4-Nitrobenzylideneamine)phenol

Synthesis of solvatochromic merocyanine dyes and their immobilization to polymers

Synthesis of 1,8–Naphthyridines and Their Application in the Development of Anionic Fluorogenic Chemosensors

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