Diazo and diazonium compounds for surface modification

Wang, Dandan; Khan, Muhammad Kamran; Moloney, Mark G.

doi:10.1016/j.tetlet.2020.151672

Cited by 20 publications

(12 citation statements)

References 97 publications

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“…Several recent reviews and papers have surveyed the advances in the development and application of diazonium compounds for the surface modification of diverse materials application of diazonium compounds for the surface modification of various materials, such as graphene, ,− electrode surfaces, − carbon nanotubes, − nanostructured mesoporous ITO films, glycosides, and graphene oxide. , Mainly, a range of aryl functional groups can be employed to functionalize the basal plane of MoS 2 through diazonium-based chemistry. − Several elegant reviews have recently focused on modifying functional materials and bioactive molecules by using aryl diazonium salts. In this section, we will just give a brief instruction toward the recent advances in this area.…”

Section: Aryl Diazonium Salts In the Modification Of Functional Mater...mentioning

confidence: 99%

“…Except for a traditional flow protocol and the merging of the photoredox/flow process, a mechanochemical synthetic route was developed using a jacketed screw reactor, allowing the synthesis of the azo compounds with β-napththol under continuous-flow conditions. Several recent reviews and papers have surveyed the advances in the development and application of diazonium compounds for the surface modification of diverse materials application of diazonium compounds for the surface modification of various materials, 461 such as graphene, 22,462−464 electrode surfaces, 465−469 carbon nanotubes, 470−477 nanostructured mesoporous ITO films, 478 glycosides, 479 and graphene oxide. 480,481 Mainly, a range of aryl functional groups can be employed to functionalize the basal plane of MoS 2 through diazonium-based chemistry.…”

Section: Aryl Diazonium Salts In Flow Chemistrymentioning

confidence: 99%

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Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

et al. 2021

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Aryl diazonium salts are versatile building blocks in organic synthesis. In light of the ever-increasing importance of aryl diazonium salts spanning most disciplines of the chemical sciences, we review the recent development of aryl diazonium chemistry over the past seven years (2013−2020). Special emphasis is put on various new transformations involving the generation of radical intermediates via thermal, photochemical, and electrochemical means. Recent advances in the development of transition metal-catalyzed reactions using aryl diazonium salts are also reviewed. Together, these newly developed transformations significantly expand the synthetic chemist's repertoire of aromatic carbon−carbon and carbon−heteroatom bond forming methods using aryl diazonium precursors, providing powerful tools for the synthesis and modification of complex molecular scaffolds.

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Section: Aryl Diazonium Salts In the Modification Of Functional Mater...mentioning

confidence: 99%

Section: Aryl Diazonium Salts In Flow Chemistrymentioning

confidence: 99%

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

et al. 2021

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“…However, aryl diazonium coupling, extensively used in functionalizing GO, was successful in preventing aggregation and maintaining single layer characteristics as evidenced by the polarized optical microscopy (POM) image of concentrated Fc-GO which displays nematic liquid crystal features (Figure 2D). [41,42] Additionally, atomic force microscopy imaging shows that large sheets sizes are maintained (20 µm average, Figure S1, Supporting Information) with an increase in thickness from 0.8-1.2 nm for GO to 1.4-1.8 nm for Fc-GO, an indicator of successful functionalization. Following washing with acetone and resuspension in 50% acetone, the solution was darker in color, but translucent and uniform, without aggregation.…”

Section: Fc-rgo Fiber Fabrication/characterizationmentioning

confidence: 99%

Dry Spun, Bulk‐Functionalized rGO Fibers for Textile Integrated Potentiometric Sensors

Napier

Matzeu

Presti

et al. 2021

Adv Materials Technologies

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biomarkers during exercise, training, or personal health monitoring. [1][2][3] Sweat is of particular interest as a target fluid given its easy access and the wealth of information contained in it, including various salts, proteins, and hormones, that reflect both the transient and chronic health status of an individual. [3] Planar, "tattoo" format electrochemical sensors have demonstrated great promise in monitoring and elucidating trends in many of the constituent compounds in sweat. [4] Transitioning these sensing configurations to a fiber-based format could offer seamless integration throughout a textile, allowing for simultaneous measurements across muscle groups and different sweat regions with increased comfort for the individual. Fiber-based sensors allow for readout and sensor locations to be independent, enabling distributed sensing in textile with a single readout interface. [5] Carbon dipped thread-based sensors were the first demonstration of ion-selective electrodes (ISEs) in a flexible 1-D textile format and continue to be improved. [6][7][8][9] The desire for smaller diameter sensors has pushed material needs beyond carboncoated threads or filaments. Recent fiber-based ion-selective sensors have used various electrode materials, including carbon nanotube fibers, gold nanowire impregnated elastomeric fibers, and conductive polymer-based fibers. [1,[10][11][12] These materials are costly to produce and, in some cases, present health and environmental concerns. [13] A promising alternative is the use of reduced graphene oxide (rGO) fibers, as they can be produced from inexpensive and abundant graphite flakes without additional binders, to realize a mechanically strong electrode with a near-pristine electrochemically active surface that can be tailored for the sensing application, and are less prone to swelling in aqueous environments than coated threads or fibers. [14][15][16][17][18] While short segments of these rGO fibers have been used as temperature sensors, gas sensors, and benchtop hydrogen peroxide sensors, they have yet to be applied to wearable sweat sensing. [19][20][21][22] rGO fibers have a wide electrochemical window (−0.9V to 1V), excellent mechanical properties, strong chemical resistance, and biocompatibility, all of which make them ideal to generate fiber-based sensors for wearable or implantable electrochemical applications. [14,20,23] Additionally, graphene oxide (GO) offers many functional groups, including epoxy and hydroxyl groups, enabling facile grafting of chemical modifiers or nanoparticles Thread or fiber-based sensors can be integrated into wearable textiles paving the way for re-engineered electrochemical sensing units for exercise or training analytics in real-time. Textile-based sensors currently have limitations such as large diameters, low conductivity, poor electrochemical performance and sensing stability, or expensive manufacturing processes-preventing many commercial applications in sweat sensing. Pure reduced graphene oxide (rGO) fibers show much promise as low-...

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“…The active carbene exhibits strong reactivity toward R–H (R = C, − N, , O, S, and B , ) bonds under mild conditions (Scheme B). The diazo and diazirine moiety can be activated thermally, − photochemically, − or under transition-metal-catalyzed conditions, , forming active carbenes to react with organic substrates by R–H activation and insertion. Therefore, we propose a carbene-mediated polymer cross-linking strategy using compounds that contain two or more carbene precursors.…”

Section: Introductionmentioning

confidence: 99%

Carbene-Mediated Polymer Cross-Linking with Diazo Compounds by C–H Activation and Insertion

Yang

Yun

et al. 2022

Macromolecules

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Compared with linear thermoplastic polymers, thermoset polymers with three-dimensional network structures exhibit improved solvent tolerance, heat resistance, and mechanical strength. The radicalmediated process is widely used to cross-link the linear polymer chains; however, this process requires high temperature (>150 °C) or UV irradiation to generate highly energetic radicals, unavoidably leading to undesired side reactions and uncontrolled cross-linking behavior. This work proposes and achieves a carbene-mediated polymer cross-linking with diazo-based compounds by C−H activation and an insertion mechanism under relatively mild conditions. A simple route containing only one or two steps is established to synthesize three generations of diazo-based cross-linkers 1G, 2G, and 3G. The cross-linker 1G exhibits the lowest cross-linking efficiency due to the undesired self-coupling of carbenes. After optimizing the chemical structure and increasing the numbers of diazo moieties, the cross-linking efficiency significantly improves for 2G and 3G cross-linkers. These cross-linkers are applicable for any polymers containing C−H bonds. They are useful in a wide range of applications, from the adhesion of low surface energy ultrahigh molecular weight polyethylene (UHMWPE) to polymer modification by co-cross-linking. This versatile, convenient, and practical carbene-mediated cross-linking strategy provides new opportunities for modification, cross-linking, and adhesion in polymer science.

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Diazo and diazonium compounds for surface modification

Cited by 20 publications

References 97 publications

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

Recent Development of Aryl Diazonium Chemistry for the Derivatization of Aromatic Compounds

Dry Spun, Bulk‐Functionalized rGO Fibers for Textile Integrated Potentiometric Sensors

Carbene-Mediated Polymer Cross-Linking with Diazo Compounds by C–H Activation and Insertion

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