Copper complexes of dopa. Control of the bonding mode

Kwik, W.L.; Purdy, Evelyn; Stiefel, Edward I.

doi:10.1021/ja00812a083

Cited by 22 publications

(13 citation statements)

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“…The concentration of free Cu 2+ ions is estimated to be 22 n m by chemical equilibrium modeling. In the heterogeneous process, Cu 2+ ions are adsorbed by the active sites provided by the catecholamine group in pDA layers, then the adsorbed Cu 2+ ions are chemically reduced to metallic Cu by borane dimethylamine complex (DMAB) in neutral media. The process can be expressed by two half reactions as below:

\begin{matrix} left \\ {3Cu}^{2+} + {6e}^{-} \to 3Cu \\ 2 {({CH}_{3})}_{2} NH : {BH}_{3} + {6H}_{2} O \to {2H}_{3} {BO}_{3} + {6H}^{+} + 2 {({CH}_{3})}_{2} NH \\ + {3H}_{2} + {6e}^{-} \end{matrix}

…”

Section: Resultsmentioning

confidence: 99%

“…The bath additive EDTA sequesters Cu 2+ ions to form a chelated compound [CuEDTA] 2− . In the heterogeneous process, Cu 2+ ions are adsorbed by the active sites provided by the catecholamine group in pDA layers, [40] then the adsorbed Cu 2+ ions are chemically reduced to metallic Cu by borane dimethylamine complex (DMAB) in neutral media. [26] Thus, with the same reducing agent, the reduction of [CuEDTA] 2− to Cu 0 is Adv.…”

Section: Cu Deposition On Polymer Nanofibersmentioning

confidence: 99%

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Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Jiang

Pan

et al. 2019

Adv Elect Materials

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Electro‐conductive nanofiber networks have potential applications as gas diffusion electrodes (GDEs) operating at solid–liquid–gas three‐phase interfaces. Flexible GDEs are developed, based on a versatile method of conformally coating a Cu layer on membranes consisting of stacked electrospun nonconductive polymer nanofibers. The Cu coating, comprising fine‐grained Cu crystals, has an average thickness of circa 50 nm and a root‐mean‐square roughness of circa 5.3 nm, maintaining the topography of polymer nanofibers. For nanofiber membranes with a thickness ranging in a few micrometers, the conformal Cu layer coats all nanofibers in the outermost layers as well as in the bulk of the membrane. All demonstrated Cu‐coated nanofiber networks have sheet resistance <2.4 Ω◽, and gas permeability in the order of 10−13 to 10−15 m2, which are comparable to some commercialized carbon based micro‐/nanofiber GDEs. Particularly, these conductive nanofiber networks have excellent bending durability, with negligible conductivity degradation after 10 000 bending test cycles. The high conductivity, gas permeability, and flexibility of these 3D nanofiber networks allow for applications as GDEs into various flexible electrochemical devices.

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\begin{matrix} left \\ {3Cu}^{2+} + {6e}^{-} \to 3Cu \\ 2 {({CH}_{3})}_{2} NH : {BH}_{3} + {6H}_{2} O \to {2H}_{3} {BO}_{3} + {6H}^{+} + 2 {({CH}_{3})}_{2} NH \\ + {3H}_{2} + {6e}^{-} \end{matrix}

…”

Section: Resultsmentioning

confidence: 99%

Section: Cu Deposition On Polymer Nanofibersmentioning

confidence: 99%

Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Jiang

Pan

et al. 2019

Adv Elect Materials

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“…However, similar bands have been observed in the Raman spectra of coat proteins of pfl and fd virions and it has been suggested that these bands arise from alanine residue in the right handed a-helical form (26). The complexes of copper adrenalin and noradrenaline at p H 5.5 can be represented by 7, which is comparable with L-Dopa copper complex at p H 6.4 (27).…”

Section: Raman Spectramentioning

confidence: 55%

Electronic and Raman spectroscopic studies of copper adrenalin complexes and copper induced compounds

Rahaman¹,

Korenkiewicz²

1976

Can. J. Chem.

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Electronic and Raman spectra of adrenalin–copper(II) complexes and copper catalyzed compounds have been studied. Adrenalin reacts with copper(II) ion at pH 9.2 and higher to produce a very short lived violet free radical, a brown adrenochrome, a yellow conjugated salt, indolyl-indoquinone, and melanin. Results indicate that copper does not form complexes with adrenalin in basic solution. Between pH 6.5 and 8.5 adrenalin transforms into adrenochrome in presence of copper. The adrenochrome in 1.5 N hydrochloric acid produces the conjugate salt that is produced in the solution of high pH. At low pH values, between pH 4.0 to 5.5, adrenalin forms a brown complex with copper(II). Copper is entirely chelated to the phenolic groups of the amines. The complex in 1.5 N hydrochloric acid produces a black polymeric pigment.

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“…The two copper complexes on the right belong to the asymmetric unit and the two complexes on the left are related by a translation of (0, 0, 1). isolated from a reaction of CuCl 2 with d,l-DOPA in water at pH 5 (Kwik et al, 1974). The authors stated that electronic properties were consistent with an N,O-trans-coordination environment, but no further details were provided.…”

Section: Resultsmentioning

confidence: 99%

“…A homoleptic copper(II) complex of racemic DOPA was isolated nearly 50 years ago (Kwik et al, 1974), but never structurally characterized. In the initial stages of a titration of a Cu II -l-DOPA solution, it was shown that the primary species was a copper ion bound to l-DOPA anions as a substituted glycinate (Boggess & Martin, 1975).…”

Section: Introductionmentioning

confidence: 99%

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

et al. 2021

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The crystal structure of the cis isomer of cis-bis(L-DOPA-κ2 N,O)copper(II) monohydrate (L-DOPA is 3,4-dihydroxy-L-phenylalanine) (CuLD), [Cu(C9H10NO4)2]·H2O, is a singular example of a structurally characterized, homoleptic, crystalline metal L-DOPA complex. CuLD crystallizes in the space group P21, with Z′ = 2. The two independent molecules are square planar, and are interconnected by a linear hydrogen-bonded chain containing 12 independent hydrogen bonds. The copper ions in both molecules have weak apical intermolecular Cu...O interactions [2.739 (2) and 2.973 (2) Å] with catechol –OH groups. A survey of the Cambridge Structural Database suggested that cis and trans isomers of Cu(NH2–C–CO2)2 amino acid complexes are equally likely to occur. 12 strong O—H...O and N—H...O hydrogen bonds stabilize an unusual linear arrangement of the Cu complexes. The Cu...Cu′ distances along the chain are nearly equal [5.0739 (3) and 5.1107 (3) Å] and the Cu...Cu′...Cu angles are nearly linear [176.75 (1)°]. The MATCH procedure available in the Oxford University Crystals for Windows package was used to carry out a detailed analysis of the relationship between the two independent molecules. MATCH has some particular advantages in studying the details of pseudosymmetry, which include: (i) no atomic-order requirements; (ii) the pseudosymmetry matrix is readily available, which allows quick insight into the symmetry elements involved and their location; and (iii) the differences between molecular centroids, as well as between all atomic positions and torsion angles, are listed. A tutorial presentation is designed to attract new users to the technique. In the present case, a search for a pseudosymmetric relationship between the two independent molecules showed that they are related by a pseudo-42 axis along the crystallographic c direction. A detailed analysis shows that the pseudo-42 symmetry is disrupted by torsions about the CH2—C(ipso) bonds, and that there is no supergroup that can be used to describe the crystal structure.

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Copper complexes of dopa. Control of the bonding mode

Cited by 22 publications

References 1 publication

Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Electronic and Raman spectroscopic studies of copper adrenalin complexes and copper induced compounds

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

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Copper complexes of dopa. Control of the bonding mode

Cited by 22 publications

References 1 publication

Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Conformal Cu Coating on Electrospun Nanofibers for 3D Electro‐Conductive Networks

Electronic and Raman spectroscopic studies of copper adrenalin complexes and copper induced compounds

cis-Bis(L-DOPA-κ2 N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry

Contact Info

Product

Resources

About

cis-Bis(L-DOPA-κ² N,O)copper(II) monohydrate: synthesis, crystal structure, and approaches to the analysis of pseudosymmetry