Copper-assisted oxidation of catechols into quinone derivatives

Gómez-Herrero, Ana Cristina; Sánchez‐Sánchez, Carlos; Cherioux, Frédéric; Martínez, José I.; Abad, José Antonio; Floreano, Luca; Cossaro, Albano; Mazaleyrat, Estelle; Guisset, Valérie; David, Philippe; Lisi, Simone; Gago, José Ángel Martín; Coraux, Johann

doi:10.1039/d0sc04883f

Cited by 20 publications

(16 citation statements)

References 64 publications

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“…Above a certain temperature indeed, molecules will desorb from the surface and/or decompose. These processes are already prominent at 630 K on Cu(111) and at 510 K on Ag(111). Before that, it is indeed possible to observe on Ag(111) and in a very narrow temperature window (∼500 K) a honeycomb phase that has been coined P3 in previous works and on Cu(111) (610 K annealing) a kind of molecular arrangement featuring units with no resemblance to the original HHTP molecules (see Figure S2 of the Supporting Information), suggesting thermal decomposition of the molecules.…”

Section: Resultsmentioning

confidence: 96%

“…The 2,3,6,7,10,11-hexahydroxytriphenylene (HHTP) molecule is made of a triphenylene core surrounded by six hydroxyl groups. This molecule is a model compound to investigate electron transfers induced between oxygen moieties attached to an aryl group (i.e., phenol) and single-crystal surfaces such as Cu(111) or Ag(111), , a process that is reminiscent of those occurring, for example, in biological cells , or energy applications. , We have analyzed the effect of this electron transfer onto the self-assembly of HHTP on Ag(111) and Cu(111) at different temperatures of deposition.…”

Section: Resultsmentioning

confidence: 99%

“…This precursor is thus particularly well suited for creating surface-supported MOFs. The supramolecular self-assembly of HHTP and the related dehydrogenation reaction on metal single-crystal surfaces have been extensively studied. ,,− Here, we show that metal–organic structures can form on the Ag(111) and Cu(111) surfaces, with different stabilities depending on the substrate nature and on the dehydrogenation level.…”

Section: Introductionmentioning

confidence: 82%

“…Starting from alcohols, such oxidation (or dehydrogenation reaction) is straightforward on copper surfaces − but also partially occurs on silver ,− and gold surfaces . A peculiar kind of alcohol, the hexahydroxytriphenylene (HHTP) molecule, has attracted much attention in this respect.…”

Section: Introductionmentioning

confidence: 99%

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Role of the Structure and Reactivity of Cu and Ag Surfaces in the Formation of a 2D Metal–Hexahydroxytriphenylene Network

et al. 2021

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We have investigated the role played by the atomic structure and reactivity of the supporting Ag(111) and Cu(111) surfaces on the formation of 2D metal–organic networks (2D-MONs) involving metal adatom clusters spawned by these two surfaces. While the hexahydroxytriphenylene (HHTP) molecule forms complexes with Ag3 and Cu3 adatom clusters on, respectively, the Ag(111) and Cu(111) surfaces, an extended order is only observed in the 2D-MON on Ag(111). By combining scanning tunneling microscopy measurements, density functional theory calculations, and microscopy image simulations, we show that the formation of Ag–HHTP metal–organic complexes is structurally compatible with a periodic arrangement of HHTP on the Ag(111) surface. In contrast, on Cu(111), tightly bonded and localized Cu–HHTP motifs are stabilized by the interaction of Cu adclusters with HHTP. However, they cannot match the surface structure of Cu(111) to form an extended 2D-MON. We observed that the formation of large 2D-MON domains on a metallic surface is only possible when the periodicity of the adsorbed surface assembly is weakly perturbed by the addition of metal adclusters that reinforced the bonding.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 82%

Section: Introductionmentioning

confidence: 99%

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Role of the Structure and Reactivity of Cu and Ag Surfaces in the Formation of a 2D Metal–Hexahydroxytriphenylene Network

et al. 2021

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“…Pyroptosis is caused by copper ion through Fenton/Haber Weiss reactions that occur and involve destructive cell death mediated by ROS [123,124]. Cuproptosis mainly occurs in cells with high energy demand and abundant mitochondria.…”

Section: Cuproptosismentioning

confidence: 99%

The Molecular Mechanisms of Defective Copper Metabolism in Diabetic Cardiomyopathy

Cui

Wang

Liu

et al. 2022

Oxidative Medicine and Cellular Longevity

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Copper is an essential trace metal element that significantly affects human physiology and pathology by regulating various important biological processes, including mitochondrial oxidative phosphorylation, connective tissue crosslinking, and antioxidant defense. Copper level has been proved to be closely related to the morbidity and mortality of cardiovascular diseases such as atherosclerosis, heart failure, and diabetic cardiomyopathy (DCM). Copper deficiency can induce cardiac hypertrophy and aggravate cardiomyopathy, while copper excess can mediate various types of cell death, such as autophagy, apoptosis, cuproptosis, pyroptosis, and cardiac hypertrophy and fibrosis. Both copper excess and copper deficiency lead to redox imbalance, activate inflammatory response, and aggravate diabetic cardiomyopathy. This defective copper metabolism suggests a specific metabolic pattern of copper in diabetes and a specific role in the pathogenesis and progression of DCM. This review is aimed at providing a timely summary of the effects of defective copper homeostasis on DCM and discussing potential underlying molecular mechanisms.

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Self‐Assembly and Oriented Growth of Conductive Ni‐CAT‐1 Metal‐Organic Framework at Solid–Liquid Interfaces

Shin

Tao

Canfield

et al. 2022

Adv Materials Inter

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Two‐dimensional (2D) conductive metal‐organic frameworks (MOF) represent a unique class of electrode materials with high capacity and power density. Understanding molecular mechanisms and pathways for heterogeneous nucleation of 2D π‐conjugated MOFs is highly desirable for controlling the structure and properties of conductive MOFs on solid substrates. Herein, a systematic study of nucleation and growth of 2D π‐conjugated Ni‐catecholate (Ni‐CAT‐1) MOFs on highly oriented pyrolytic graphite (HOPG) and copper substrates is reported. It is discovered that the nucleation density and growth kinetics of the MOF film can be controlled by varying substrate interactions with the organic linker. Specifically, π–π interactions between the linker and the HOPG dictate lower nucleation density, whereas π–metal interactions between the linker and the copper substrate dictate faster nucleation and higher nucleation densities. These studies reveal the key mechanism for Ni‐CAT‐1 nucleation on different surfaces and provide insights into interfacial control over the growth of other 2D π‐conjugated MOF films on solid substrates to inform synthesis of functional materials.

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Copper-assisted oxidation of catechols into quinone derivatives

Abstract: An antioxidant catechol transforms following intramolecular redox reactions into highly reactive oxygen species, a semiquinone and a quinone, on copper.

Cited by 20 publications

References 64 publications

Role of the Structure and Reactivity of Cu and Ag Surfaces in the Formation of a 2D Metal–Hexahydroxytriphenylene Network

Role of the Structure and Reactivity of Cu and Ag Surfaces in the Formation of a 2D Metal–Hexahydroxytriphenylene Network

The Molecular Mechanisms of Defective Copper Metabolism in Diabetic Cardiomyopathy

Self‐Assembly and Oriented Growth of Conductive Ni‐CAT‐1 Metal‐Organic Framework at Solid–Liquid Interfaces

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