High-Yield Alkylation and Arylation of Graphene via Grignard Reaction with Fluorographene

. 2017 Feb 14 ; 29 (3) : 926-930. [epub] 20170129

Status PubMed-not-MEDLINE Jazyk angličtina Země Spojené státy americké Médium print-electronic

Typ dokumentu časopisecké články

Perzistentní odkaz   https://www.medvik.cz/link/pmid28216805

Zobrazit více v PubMed

Georgakilas V.; Otyepka M.; Bourlinos A. B.; Chandra V.; Kim N.; Kemp K. C.; Hobza P.; Zbořil R.; Kim K. S. Functionalization of Graphene: Covalent and Non-Covalent Approaches, Derivatives and Applications. Chem. Rev. 2012, 112, 6156–6214. 10.1021/cr3000412. PubMed DOI

Criado A.; Melchionna M.; Marchesan S.; Prato M. The Covalent Functionalization of Graphene on Substrates. Angew. Chem., Int. Ed. 2015, 54, 10734–10750. 10.1002/anie.201501473. PubMed DOI

Eigler S.; Hirsch A. Chemistry with Graphene and Graphene Oxide—Challenges for Synthetic Chemists. Angew. Chem., Int. Ed. 2014, 53, 7720–7738. 10.1002/anie.201402780. PubMed DOI

Jeon I.-Y.; Bae S.-Y.; Seo J.-M.; Baek J.-B. Scalable Production of Edge-Functionalized Graphene Nanoplatelets via Mechanochemical Ball-Milling. Adv. Funct. Mater. 2015, 25, 6961–6975. 10.1002/adfm.201502214. DOI

Baraket M.; Walton S. G.; Lock E. H.; Robinson J. T.; Perkins F. K. The Functionalization of Graphene Using Electron-Beam Generated Plasmas. Appl. Phys. Lett. 2010, 96, 231501.10.1063/1.3436556. DOI

Lee W. H.; Suk J. W.; Lee J.; Hao Y.; Park J.; Yang J. W.; Ha H.-W.; Murali S.; Chou H.; Akinwande D.; Kim K. S.; Ruoff R. S. Simultaneous Transfer and Doping of CVD-Grown Graphene by Fluoropolymer for Transparent Conductive Films on Plastic. ACS Nano 2012, 6, 1284–1290. 10.1021/nn203998j. PubMed DOI

Lee W. H.; Suk J. W.; Chou H.; Lee J.; Hao Y.; Wu Y.; Piner R.; Akinwande D.; Kim K. S.; Ruoff R. S. Selective-Area Fluorination of Graphene with Fluoropolymer and Laser Irradiation. Nano Lett. 2012, 12, 2374–2378. 10.1021/nl300346j. PubMed DOI

Wang Q. H.; Jin Z.; Kim K. K.; Hilmer A. J.; Paulus G. L. C.; Shih C.-J.; Ham M.-H.; Sanchez-Yamagishi J. D.; Watanabe K.; Taniguchi T.; Kong J.; Jarillo-Herrero P.; Strano M. S. Understanding and Controlling the Substrate Effect on Graphene Electron-Transfer Chemistry via Reactivity Imprint Lithography. Nat. Chem. 2012, 4, 724–732. 10.1038/nchem.1421. PubMed DOI

Fan X.; Nouchi R.; Tanigaki K. Effect of Charge Puddles and Ripples on the Chemical Reactivity of Single Layer Graphene Supported by SiO2/Si Substrate. J. Phys. Chem. C 2011, 115, 12960–12964. 10.1021/jp202273a. DOI

Sharma R.; Baik J. H.; Perera C. J.; Strano M. S. Anomalously Large Reactivity of Single Graphene Layers and Edges toward Electron Transfer Chemistries. Nano Lett. 2010, 10, 398–405. 10.1021/nl902741x. PubMed DOI PMC

Koehler F. M.; Jacobsen A.; Ensslin K.; Stampfer C.; Stark W. J. Selective Chemical Modification of Graphene Surfaces: Distinction Between Single- and Bilayer Graphene. Small 2010, 6, 1125–1130. 10.1002/smll.200902370. PubMed DOI

Diankov G.; Neumann M.; Goldhaber-Gordon D. Extreme Monolayer-Selectivity of Hydrogen-Plasma Reactions with Graphene. ACS Nano 2013, 7, 1324–1332. 10.1021/nn304903m. PubMed DOI

Nair R. R.; Ren W.; Jalil R.; Riaz I.; Kravets V. G.; Britnell L.; Blake P.; Schedin F.; Mayorov A. S.; Yuan S.; Katsnelson M. I.; Cheng H.-M.; Strupinski W.; Bulusheva L. G.; Okotrub A. V.; Grigorieva I. V.; Grigorenko A. N.; Novoselov K. S.; Geim A. K. Fluorographene: A Two-Dimensional Counterpart of Teflon. Small 2010, 6, 2877–2884. 10.1002/smll.201001555. PubMed DOI

Zbořil R.; Karlický F.; Bourlinos A. B.; Steriotis T. A.; Stubos A. K.; Georgakilas V.; Šafářová K.; Jančík D.; Trapalis C.; Otyepka M. Graphene Fluoride: A Stable Stoichiometric Graphene Derivative and Its Chemical Conversion to Graphene. Small 2010, 6, 2885–2891. 10.1002/smll.201001401. PubMed DOI PMC

Robinson J. T.; Burgess J. S.; Junkermeier C. E.; Badescu S. C.; Reinecke T. L.; Perkins F. K.; Zalalutdniov M. K.; Baldwin J. W.; Culbertson J. C.; Sheehan P. E.; Snow E. S. Properties of Fluorinated Graphene Films. Nano Lett. 2010, 10, 3001–3005. 10.1021/nl101437p. PubMed DOI

Nair R. R.; Sepioni M.; Tsai I.-L.; Lehtinen O.; Keinonen J.; Krasheninnikov A. V.; Thomson T.; Geim A. K.; Grigorieva I. V. Spin-Half Paramagnetism in Graphene Induced by Point Defects. Nat. Phys. 2012, 8, 199–202. 10.1038/nphys2183. DOI

Karlický F.; Kumara R. D.; Otyepka M.; Zbořil R. Halogenated Graphenes: Rapidly Growing Family of Graphene Derivatives. ACS Nano 2013, 7, 6434–6464. 10.1021/nn4024027. PubMed DOI

Feng W.; Long P.; Feng Y.; Li Y. Two-Dimensional Fluorinated Graphene: Synthesis, Structures, Properties and Applications. Adv. Sci. 2016, 3, 150041310.1002/advs.201500413. PubMed DOI PMC

Dubecký M.; Otyepková E.; Lazar P.; Karlický F.; Petr M.; Čépe K.; Banáš P.; Zbořil R.; Otyepka M. Reactivity of Fluorographene: A Facile Way toward Graphene Derivatives. J. Phys. Chem. Lett. 2015, 6, 1430–1434. 10.1021/acs.jpclett.5b00565. PubMed DOI

Urbanová V.; Holá K.; Bourlinos A. B.; Čépe K.; Ambrosi A.; Loo A. H.; Pumera M.; Karlický F.; Otyepka M.; Zbořil R. Thiofluorographene-Hydrophilic Graphene Derivative with Semiconducting and Genosensing Properties. Adv. Mater. 2015, 27, 2305–2310. 10.1002/adma.201500094. PubMed DOI

Stine R.; Ciszek J. W.; Barlow D. E.; Lee W.-K.; Robinson J. T.; Sheehan P. E. High-Density Amine-Terminated Monolayers Formed on Fluorinated CVD-Grown Graphene. Langmuir 2012, 28, 7957–7961. 10.1021/la301091f. PubMed DOI

Whitener K. E. Jr.; Stine R.; Robinson J. T.; Sheehan P. E. Graphene as Electrophile: Reactions of Graphene Fluoride. J. Phys. Chem. C 2015, 119, 10507–10512. 10.1021/acs.jpcc.5b02730. DOI

Bosch-Navarro C.; Walker M.; Wilson N. R.; Rourke J. P. Covalent Modification of Exfoliated Fluorographite with Nitrogen Functionalities. J. Mater. Chem. C 2015, 3, 7627–7631. 10.1039/C5TC01633A. DOI

Li B.; He T.; Wang Z.; Cheng Z.; Liu Y.; Chen T.; Lai W.; Wang X.; Liu X. Chemical Reactivity of C-F Bonds Attached to Graphene with Diamines Depending on Their Nature and Location. Phys. Chem. Chem. Phys. 2016, 18, 17495–17505. 10.1039/C6CP01929C. PubMed DOI

Lazar P.; Chua C. K.; Holá K.; Zbořil R.; Otyepka M.; Pumera M. Dichlorocarbene-Functionalized Fluorographene: Synthesis and Reaction Mechanism. Small 2015, 11, 3790–3796. 10.1002/smll.201500364. PubMed DOI

Ye X.; Ma L.; Yang Z.; Wang J.; Wang H.; Yang S. Covalent Functionalization of Fluorinated Graphene and Subsequent Application as Water-Based Lubricant Additive. ACS Appl. Mater. Interfaces 2016, 8, 7483–7488. 10.1021/acsami.5b10579. PubMed DOI

Boul P. J.; Liu J.; Mickelson E. T.; Huffman C. B.; Ericson L. M.; Chiang I. W.; Smith K. A.; Colbert D. T.; Hauge R. H.; Margrave J. L.; Smalley R. E. Reversible Sidewall Functionalization of Buckytubes. Chem. Phys. Lett. 1999, 310, 367–372. 10.1016/S0009-2614(99)00713-7. DOI

Hossain M. Z.; Razak M. B. A.; Noritake H.; Shiozawa Y.; Yoshimoto S.; Mukai K.; Koitaya T.; Yoshinobu J.; Hosaka S. Monolayer Selective Methylation of Epitaxial Graphene on SiC(0001) through Two-Step Chlorination–Alkylation Reactions. J. Phys. Chem. C 2014, 118, 22096–22101. 10.1021/jp5068186. DOI

Hossain M. Z.; Razak M. B. A. Halogenation of Epitaxial Graphene Grown on the Si-Face of the SiC(0001) Substrate and Its Further Reaction with Grignard Reagent. New J. Chem. 2016, 40, 1671–1678. 10.1039/C5NJ02642C. DOI

Bourlinos A. B.; Šafářová K.; Šišková K.; Zbořil R. The Production of Chemically Converted Graphenes from Graphite Fluoride. Carbon 2012, 50, 1425–1428. 10.1016/j.carbon.2011.10.012. DOI

Englert J. M.; Dotzer C.; Yang G.; Schmid M.; Papp C.; Gottfried J. M.; Steinrück H.-P.; Spiecker E.; Hauke F.; Hirsch A. Covalent Bulk Functionalization of Graphene. Nat. Chem. 2011, 3, 279–286. 10.1038/nchem.1010. PubMed DOI

Englert J. M.; Vecera P.; Knirsch K. C.; Schäfer R. A.; Hauke F.; Hirsch A. Scanning-Raman-Microscopy for the Statistical Analysis of Covalently Functionalized Graphene. ACS Nano 2013, 7, 5472–5482. 10.1021/nn401481h. PubMed DOI

Karlický F.; Zbořil R.; Otyepka M. Band Gaps and Structural Properties of Graphene Halides and Their Derivates: A Hybrid Functional Study with Localized Orbital Basis Sets. J. Chem. Phys. 2012, 137, 034709.10.1063/1.4736998. PubMed DOI

Karlický F.; Otyepka M. Band Gaps and Optical Spectra of Chlorographene, Fluorographene and Graphane from G0W0, GW0 and GW Calculations on Top of PBE and HSE06 Orbitals. J. Chem. Theory Comput. 2013, 9, 4155–4164. 10.1021/ct400476r. PubMed DOI

Lomeda J. R.; Doyle C. D.; Kosynkin D. V.; Hwang W.-F.; Tour J. M. Diazonium Functionalization of Surfactant-Wrapped Chemically Converted Graphene Sheets. J. Am. Chem. Soc. 2008, 130, 16201–16206. 10.1021/ja806499w. PubMed DOI

Zhu Y.; Higginbotham A. L.; Tour J. M. Covalent Functionalization of Surfactant-Wrapped Graphene Nanoribbons. Chem. Mater. 2009, 21, 5284–5291. 10.1021/cm902939n. DOI

Wei J.; Qiu J. Allyl-Functionalization Enhanced Thermally Stable Graphene/Fluoroelastomer Nanocomposites. Polymer 2014, 55, 3818–3824. 10.1016/j.polymer.2014.06.063. DOI

Rodier B. J.; Mosher E. P.; Burton S. T.; Matthews R.; Pentzer E. Polythioether Particles Armored with Modifiable Graphene Oxide Nanosheets. Macromol. Rapid Commun. 2016, 37, 894–899. 10.1002/marc.201600093. PubMed DOI

Roy S.; Das T.; Zhang L.; Hu X. M. Harnessing the Maximum Reinforcement of Graphene Oxide for Poly(vinylidene Fluoride) Nanocomposites via Polydopamine Assisted Novel Surface Modification. RSC Adv. 2016, 6, 69919–69929. 10.1039/C6RA12997H. DOI

Nejnovějších 20 citací...

Zobrazit více v
Medvik | PubMed

Solvent Controlled Generation of Spin Active Polarons in Two-Dimensional Material under UV Light Irradiation

. 2024 Jun 05 ; 146 (22) : 15010-15018. [epub] 20240502

Emerging graphene derivatives as active 2D coordination platforms for single-atom catalysts

. 2022 Sep 29 ; 14 (37) : 13490-13499. [epub] 20220929

Chemical Tuning of Specific Capacitance in Functionalized Fluorographene

. 2019 Jul 09 ; 31 (13) : 4698-4709. [epub] 20190607

Alkynylation of graphene via the Sonogashira C-C cross-coupling reaction on fluorographene

. 2019 Jan 22 ; 55 (8) : 1088-1091.

2D Chemistry: Chemical Control of Graphene Derivatization

. 2018 Jul 05 ; 9 (13) : 3580-3585. [epub] 20180615

Reactivity of fluorographene is triggered by point defects: beyond the perfect 2D world

. 2018 Mar 08 ; 10 (10) : 4696-4707.

Chemistry, properties, and applications of fluorographene

. 2017 Dec ; 9 () : 60-70.

Cyanographene and Graphene Acid: Emerging Derivatives Enabling High-Yield and Selective Functionalization of Graphene

. 2017 Mar 28 ; 11 (3) : 2982-2991. [epub] 20170220

Najít záznam

Citační ukazatele

Nahrávání dat ...

Možnosti archivace

Nahrávání dat ...