A novel strategy for chromogenic chemosensors highly selective toward cyanide based on its reaction with 4-(2,4-dinitrobenzylideneamino)benzenes or 2,4-dinitrostilbenes

Heying, Renata S.; Nandi, Leandro G.; Bortoluzzi, Adaílton J.; Machado, Vanderlei G.

doi:10.1016/j.saa.2014.10.041

Cited by 12 publications

(4 citation statements)

References 67 publications

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“…The copper salt [(MeCN) 4 Cu](TfO) was prepared by adapting the Kubas procedure using TfOH. 87 4-Dimethylaminonitrosobenzene (2 NMe 2 ), 88,89 4-chloronitrosobenzene (2 Cl ), 90 4-bromosonitrobenzene (2 Br ), 90 and 4-nitrosonitrobenzene (2 NO 2 ) 91 were prepared via literature procedures. Isotopically labeled 15 N-4-nitrosonitrobenzene and [(TMPDCu) 2 (μ-TfO)(μ-η 2 :η 2 -p-NO 2 -C 6 H 4 NO)](TfO) were prepared following the procedure reported earlier.…”

Section: Scheme 6 Thermodynamic Analysis Of Hat Reactivitymentioning

confidence: 99%

Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts

et al. 2020

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A series of copper/nitrosoarene complexes were created that mimic several steps in biomimetic O 2 activation by copper(I). The reaction of the copper(I) complex of N,N,N′,N′tetramethypropylenediamine with a series of para-substituted nitrosobenzene derivatives leads to adducts in which the nitrosoarene (ArNO) is reduced by zero, one, or two electrons, akin to the isovalent species dioxygen, superoxide, and peroxide, respectively. The geometric and electronic structures of these adducts were characterized by means of X-ray diffraction, vibrational analysis, ultraviolet−visible spectroscopy, NMR, electrochemistry, and density functional theory (DFT) calculations. The bonding mode of the NO moiety depends on the oxidation state of the ArNO moiety: κN for ArNO, mononuclear η 2-NO and dinuclear μ-η 2 :η 1 for ArNO •− , and dinuclear μ-η 2 :η 2 for ArNO 2−. 15 N isotopic labeling confirms the reduction state by measuring the NO stretching frequency (1392 cm −1 for κN-ArNO, 1226 cm −1 for η 2-ArNO •− , 1133 cm −1 for dinuclear μ-η 2 :η 1-ArNO •− , and 875 cm −1 for dinuclear μ-η 2 :η 2 for ArNO 2−). The 15 N NMR signal disappears for the ArNO •− species, establishing a unique diagnostic for the radical state. Electrochemical studies indicate reduction waves that are consistent with one-electron reduction of the adducts and are compared with studies performed on Cu-O 2 analogues. DFT calculations were undertaken to confirm our experimental findings, notably to establish the nature of the charge-transfer transitions responsible for the intense green color of the complexes. In fine, this family of complexes is unique in that it walks through three redox states of the ArNO moiety while keeping the metal and its supporting ligand the same. This work provides snapshots of the reactivity of the toxic nitrosoarene molecules with the biologically relevant Cu(I) ion. 47 usually too oxidative to be stable above −60°C.

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Section: Scheme 6 Thermodynamic Analysis Of Hat Reactivitymentioning

confidence: 99%

Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts

et al. 2020

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“…In many reported studies for cyanide detection, anions alone were taken in a semi aqueous medium or aqueous medium, whereas receptors were taken in pure organic medium. In some other cases, receptors had been taken in organic solvents with very little amount (1-10%) of water for increasing the selectivity for cyanide ions among other anions [14][15][16][17][18][19][20][21][22] (Table 1). To overcome this issue, we planned to design a receptor that can be soluble or solubilized by water.…”

Section: Introductionmentioning

confidence: 99%

Novel chromogenic selective sensors for aqueous cyanide ions under high water content and real sample analysis

Balamurugan

2016

Anal. Methods

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“…Similarly, a Cu(II) complex of a N-containing compound, N,N-dimethyldipyrromethane-Cu 2+ , prepared insitu by mixing the two in aqueous medium, was successfully shown to serve as a colorimetric detection agent for cyanide [44]. While other N-containing compounds such as N- (2,4- (2,4-dinitrobenzylidene)aniline, and 2,4-dinitro-40-(dimethylamino)stilbene were also shown to serve as chromogenic agents for detection of cyanide, they could do so in dimethyl sulfoxide solution [45]. Kim et al[46] have demonstrated a colorimetric cyanide chemosensor based on 6'-((1E,1'E)-hydrazine-1,2-diylidenebis(methanylylidene))bis (2,4-dichlorophenol), which resulted in color changes from colorless to yellow in aqueous solution in the presence of cyanide.…”

Section: Page 5 Of 35mentioning

confidence: 99%

Bicinchoninic acid-based colorimetric chemosensor for detection of low concentrations of cyanide

Biradar

Sun

et al. 2016

Sensors and Actuators B: Chemical

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A novel strategy for chromogenic chemosensors highly selective toward cyanide based on its reaction with 4-(2,4-dinitrobenzylideneamino)benzenes or 2,4-dinitrostilbenes

Cited by 12 publications

References 67 publications

Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts

Tuning Inner-Sphere Electron Transfer in a Series of Copper/Nitrosoarene Adducts

Novel chromogenic selective sensors for aqueous cyanide ions under high water content and real sample analysis

Bicinchoninic acid-based colorimetric chemosensor for detection of low concentrations of cyanide

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