Metal—polyelectrolyte Complexes. Viii. The Poly-N-Vinylimidazole—copper(ii) Complex

Gold, Daniel H.; Gregor, Harry P.

doi:10.1021/j100839a027

Cited by 71 publications

(38 citation statements)

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“…[2,7,12] Amines containing hydroxamic acid or 3-hydroxy-2-pyridinone were prepared using unexceptional chemistry, and then coupled to the active ester groups on 2. In a typical metal-binding experiment, 200 mg of 6 were added to 25 mL of an aqueous solution containing 15.5 ppm ferric chloride to give a red solution at 25 8C (A 0.65, l 439 nm).…”

Section: Methodsmentioning

confidence: 99%

“…The reaction also represents a rare example of a transition metal catalyzed transformation to give allenes. [6] The substrates, (Z)-2-bromo-1,3-butadienes (1), are readily available in 63 ± 90 % yield by palladium-catalyzed regio-and stereoselective cross-coupling of 1,1-dibromo-1-alkenes [7] with the corresponding vinylzinc reagents (Scheme 1). [ choice of the organometallic reagent is important for this step; while (CH 2 CH)ZnCl gives the coupling product in satisfactory yield, the less-reactive vinyltin reagent Bu 3 Sn(CH CH 2 ) gives the same product in very low yield (`20 %).…”

Section: Nu -mentioning

confidence: 99%

“…*] Prof. D. E. Bergbreiter, Dr. N. Koshti, Dr. J. G. Franchina, J. D.copolymers were prepared by copolymerization of vinyl imidazole and 1 [7,8]. Experiments like those with 5 showed that 0.15 g of 10 in 25 mL of water binds 14.4 ppm of Fe III (at 25 8C: A 1.109, l max 578 nm).…”

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confidence: 99%

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Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

et al. 2000

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Section: Methodsmentioning

confidence: 99%

Section: Nu -mentioning

confidence: 99%

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Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

et al. 2000

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“…Imidazoles are amphoteric compounds with a basic, "pyridine-type" nitrogen, and (where the NH is unsubstituted) a weakly acidic, "pyrrole-type" amino nitrogen in the ring. In consequence , imidazoles readily form salts with acids and often form salts or complexes with metals such as copper, silver, cobalt, and nickel (8)(9)(10)(11)(12)(13). One of the concerns about using HC1 for etching the polymeric films is whether a layer of polyvinylimidazole hydrochloride residue is left on the film surface after etching and thus, yielding erroneous results regarding the depth profile.…”

Section: Methodsmentioning

confidence: 99%

Chemical Depth Profiling Analysis of Polyvinylimidazole Film on Copper

Eng

Ishida

1988

J. Electrochem. Soc.

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Molecular structural changes of poly-N-vinylimidazole (PVI(1)) and poly-4(5)-vinylimidazole (PVI(4)) films by copper initiated reactions as a function of the distance from the copper surface have been studied. The chemical depth profiling analysis involves progressive etchings of the polymeric film on copper with aqueous acidic solutions of increasing concentrations and examination of the film by Fourier transform infrared reflection-absorption spectroscopy (FT-IR RAS). The result shows that the outer layer of the thermally untreated PVI(1) film consists of loosely bound or unreacted PVI(1) molecules. Relatively weak complexes with random orientation fill the middle and interfacial layers. For the thermally treated PVI(1) and PVI(4) samples, relatively weak complexes are formed at the outer layer. Cyano compounds, formed as the result of ring cleavages, are also found at the outer layer. The middle layer is made of complexes of different degrees of completeness. Loci of oxidation products are also discussed.Previous reports (1, 2) have shown that poly-N-vinylimidazole (PVI(1)) and poly-4(5)-vinylimidazole (PVI(4)) are effective corrosion inhibitors for copper at elevated temperatures. Thermal degradation studies (3, 4) were subsequently carried out to investigate the inhibition mechanism using Fourier transform infrared reflection-absorption spectroscopy (FT-IR RAS). The RAS detects the transition dipole moments only in the normal direction of the metal surface, thus one can study the orientation of molecules if the vibrational modes are known. The polymeric films deposited on copper with 150 nm in thickness and considered as relatively thick in the reflection-absorption (R-A) experiments. Thus, the R-A spectra of the sample represented various molecular structures and orientations from all parts of the film. It was also likely that the structure and orientation of the interfacial layer next to the copper might be different than the middle layer and the outer layer exposed to the air. Molecular structural changes by copper initiated reactions or oxidation as a function of the distance from the copper surface is an extremely important subject in order to understand the molecular mechanisms of anticorrosion films. Thus, depth profiling analysis yields useful information about the thickness effects of these actions.Sputtering is the most commonly used technique associated with electron spectroscopy for chemical analysis (ESCA), Auger electron spectroscopy (AES), secondary ion mass spectrometry (SIMS) and ion scattering spectroscopy (ISS). Depth profiling analysis can be done in conjunction with a noble gas ion beam for sputtering of a surface. The process involves bombardment of the specimen surface with a beam of argon or xenon ions to sputter etch the specimen surface while simultaneously bombarding the specimen with the electron beam or with an x-ray beam. However, a serious drawback of this technique is that the molecular structure or orientation changes may be induced by the instrumental requirements such as ul...

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“…the pyrrole nitrogen (see Scheme 1), e.g. poly (1-vinylimidazole) or poly(N-vinylimidazole) [11,[20][21][22][23], since the monomer is synthesised by attaching the vinyl group to the electronegative pyrrole nitrogen [24]. However in histidine, the most common naturally existing type of imidazole ligand, the imidazole is attached at the 4 th position C 4 , leaving the pyrrole nitrogen unsubstituted.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and polymerisation of maleoyl-L-histidine monomers and addition of histidine to an ethylene-alt-maleic co-polymer

2012

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This work has investigated two routes of synthesising polymers containing L-histidine using maleimide chemistry; grafting of histidine onto an ethylenealt-maleic anhydride copolymer and AIBN (azobisisobutyronitrile) initiated radical polymerisation of the monomer maleoyl-L-histidine. The grafting technique and monomer synthesis are utilising the maleimide formation between the primary amine of histidine and maleic anhydride. The reactions are conveniently carried out in one step with good yields. The copolymers containing L-histidine were prepared by reacting L-histidine or Lhistidine methyl ester with poly(ethylene-alt maleic anhydride) in DMSO at 50°C for 8-16 h with 80% yields independent of the degree of substitution. The monomer maleoyl-L-histidine was synthesised by reacting histidine and maleic anhydride in acetic acid and the monomer was subsequently polymerised by AIBN radical initiation in DMSO at 80°C for 48 h to yield poly(N-histidyl maleimide). The resulting polymer had a different optical rotation ([α] D 20 0−11) than the monomer ([α] D 20 0+25), which is ascribed to the threo-diisotactic and/or threodisyndiotactic stereoregularity of the polymer.

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Metal—polyelectrolyte Complexes. Viii. The Poly-N-Vinylimidazole—copper(ii) Complex

Cited by 71 publications

References 0 publications

Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

Sequestration of Trace Metals Using Water-Soluble and Fluorous Phase-Soluble Polymers

Chemical Depth Profiling Analysis of Polyvinylimidazole Film on Copper

Synthesis and polymerisation of maleoyl-L-histidine monomers and addition of histidine to an ethylene-alt-maleic co-polymer

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