1,3,5-Triaryl-2-penten-1,5-dione anchored to insoluble supports as heterogeneous chromogenic chemosensor

Álvaro, Mercedes; Aprile, Carmela; Corma, Avelino; Fornés, Vicente; Garcı́a, Hermenegildo; Peris, Encarna

doi:10.1016/j.tet.2004.06.090

Cited by 8 publications

(8 citation statements)

References 13 publications

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“…This is the case of alkali metal ions and alkaline-earth cations. As reported in an earlier work on PDO attached to silica particles, [13] PDO responds also to Brönsted acids. For this reason, most of the experiments in aqueous media were conducted in HEPES buffered solution at pH 5.…”

Section: Pdo-peg As a Soluble Reusable Sensorsupporting

confidence: 69%

“…[13] By controlling the pyrylium/styrene molar ratio, as well as the polymerization conditions, a co-polymer with adequate solubility in ethanol, dichloromethane, and other organic solvents, but insoluble in water, was obtained. The actual sensing form, namely the open pentenedione form, was again obtained by hydrolytic ring opening in a mixture of ethanol and water in the presence of sodium acetate as base to give PDO-PS.…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H NMR spectrum of dialyzed PDO-PEG free from PDO (as evidenced by thin-layer chromatography) shows weak signals between δ = 7.9-7.1 ppm corresponding to the aromatic protons of PDO and a signal at δ = 4.79 ppm attributable to -CH 2 -CO-Ph. Due to the relatively low PDO loading, the 13 C NMR spectrum of PDO-PEG does not show any characteristic signal of the covalently attached colorimetric sensor. Evidence for the binding between the PEG backbone and PDO was also obtained by combustion chemical analysis, IR spectroscopy, and UV/Vis spectroscopy.…”

Section: Synthesis Of 4-[4-(allylmethylamino)mentioning

confidence: 98%

“…Herein we report the preparation of a 4-(p-aminophenyl)-2,6-diphenylpent-2-ene-1,5-dione covalently attached to a water-soluble poly(ethylene glycol) and compare its performance with that of a water-insoluble, low-molecular-weight polystyrene recently prepared by us. [13] The use of soluble poly(ethylene glycol) as a scaffold for catalysts or reagents is a topic of much current interest. Their solubility properties allow the reactions to be performed in homogeneous solution in some solvents and quantitatively recover the polymer by precipitation with diethyl ether after use.…”

Section: Introductionmentioning

confidence: 99%

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A Soluble and Reusable Colorimetric Sensor Based on the Covalent Attachment of a Triarylpentenedione to Poly(ethylene glycol)

et al. 2005

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3‐(4‐Aminophenyl)‐1,5‐diphenylpent‐2‐ene‐1,5‐dione (PDO) is a colorimetric sensor of Lewis acid cations that has been covalently attached to a poly(ethylene glycol) (PEG) scaffold. The resulting PDO‐PEG is soluble in water and other organic solvents and acts as a colorimetric sensor of Lewis acid cations by undergoing cyclization into the triarylpyrylium form. In water, PDO‐PEG also undergoes the colorimetric change in the presence of Brönsted acids, which may limit its usefulness. This modified PEG is recoverable by precipitation from cold ethanol and reusable after reopening of the triarylpyrylium heterocycle to the active pentenedione form. The testing‐recovery‐reuse cycle has been performed five times without noticeable differences in the response. In contrast to PDO‐PEG, PDO on its own is insoluble in water and remains completely soluble in ethanol. This solubility behavior of PDO makes the molecule unsuitable for use as a reusable and recoverable sensor. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Section: Pdo-peg As a Soluble Reusable Sensorsupporting

confidence: 69%

Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of 4-[4-(allylmethylamino)mentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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A Soluble and Reusable Colorimetric Sensor Based on the Covalent Attachment of a Triarylpentenedione to Poly(ethylene glycol)

et al. 2005

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“…EDP and N-allyl-N-methylaniline were synthesized according to published procedures. [39] The iron and rhodium corroles were prepared as described in previous publications. [40] …”

Section: Methodsmentioning

confidence: 99%

Iron(III) Corroles and Porphyrins as Superior Catalysts for the Reactions of Diazoacetates with Nitrogen‐ or Sulfur‐Containing Nucleophilic Substrates: Synthetic Uses and Mechanistic Insights

Aviv

Gross

2008

Chemistry A European J

130

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A thorough mechanistic investigation has been performed on the reactions of primary and secondary amines with diazoacetates, which proceed uniquely quickly and efficiently when catalyzed by iron(III) corroles and porphyrins. Two major differences in relation to other metal-based catalysts are that the iron complexes are not poisoned by excess amine and that metal-carbene intermediates are apparently not involved in the reaction pathway. The results instead point towards nitrogen ylide intermediates formed by nucleophilic attack of the amines on diazoacetate-coordinated iron complexes. Nitrogen ylides are also formed when allyl- and propargyl-substituted tertiary amines react with diazoacetates, a scenario that smoothly leads to 2,3-rearrangement reaction products with catalytic amounts of the iron(III) complexes. Similar findings regarding the superiority of the iron(III) complexes (in terms of catalyst loading, chemical yields, and reaction conditions) were obtained with thiols (S--H insertion) and sulfides (2,3-rearrangement reactions), which suggest similar mechanisms operate in these cases.

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Six‐Membered Rings with One Oxygen: Pyrylium Ion, Related Systems and Benzo‐Derivatives

Santamarı́a

Valdés

2011

Modern Heterocyclic Chemistry

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1,3,5-Triaryl-2-penten-1,5-dione anchored to insoluble supports as heterogeneous chromogenic chemosensor

Cited by 8 publications

References 13 publications

A Soluble and Reusable Colorimetric Sensor Based on the Covalent Attachment of a Triarylpentenedione to Poly(ethylene glycol)

A Soluble and Reusable Colorimetric Sensor Based on the Covalent Attachment of a Triarylpentenedione to Poly(ethylene glycol)

Iron(III) Corroles and Porphyrins as Superior Catalysts for the Reactions of Diazoacetates with Nitrogen‐ or Sulfur‐Containing Nucleophilic Substrates: Synthetic Uses and Mechanistic Insights

Six‐Membered Rings with One Oxygen: Pyrylium Ion, Related Systems and Benzo‐Derivatives

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