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

Chronopoulos, Demetrios D.; Bakandritsos, Aristides; Lazar, Petr; Pykal, Martin; Čépe, Klára; Zbořil, Radek; Otyepka, Michal

doi:10.1021/acs.chemmater.6b05040

Cited by 69 publications

(57 citation statements)

References 39 publications

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“…FTIR analyses reveal that compared to FG ( Figure S2), oxygen groups in the form of ÀCOOH (1730 cm À1 ) and ÀCOH (1384 cm À1 )h ave been effectively introduced, and CÀFb onds in the form of ÀCF (1218 cm À1 )a re retained (Fig-ure 2a)· [35][36][37][38] After modification,i ti so bserved that the characteristicp eaks of CS located at 1416 cm À1 and 1599 cm À1 can be found in FGOÀCS, [41,43] and the appearance of NHÀCO stretching vibrationa t1 645 cm À1 further confirms the formation of amide bonds between CS and FGO, both of which clearlyi ndicatet he successful modification process. [36][37][38][39][40][41] As depicted in Figure 2d, the N1s andF 1s spectra of FGOÀCS also confirmst he effective graft of CS to FGO. Am ore detailed chemical nature study from C1ss pectrum in Figure 2c displays evident formation of CÀN( 286.2 eV), and the existence O=C( 288.2 eV), CÀF (289.4 eV), and ÀCF 2 (290.6 eV).…”

Section: Resultsmentioning

confidence: 99%

Functionalized Ultrasmall Fluorinated Graphene with High NIR Absorbance for Controlled Delivery of Mixed Anticancer Drugs

Gong

Zhao

Dai

et al. 2017

Chemistry A European J

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Fluorinated graphene (FG) possess distinctively novel properties different from graphene and is suitable for many biomedical applications. However, the hydrophobic nature and inert properties of FG limit its further application as a biological material. Here we show the preparation of nano-sized FG (ca. 60 nm) that exhibits high NIR absorbance for photothermal therapy. In order to make it stable in physiological solutions, the FG is enriched with oxygen and followed by covalent binding with chitosan as a novel pH-responsive nanocarrier. Furthermore, controlled loading of two anticancer drugs, doxorubicin (DOX) and camptothecin (CPT) has been realized and the functionalized ultrasmall FG shows remarkably high cytotoxicity toward Hela cancer cells compared to that loaded with either CPT or DOX only. This work established nano-sized FG as a novel photothermal agent due to its small size and can be used a stimulus-responsive nanocarrier for mixed drug delivery and combined therapy.

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Section: Resultsmentioning

confidence: 99%

Functionalized Ultrasmall Fluorinated Graphene with High NIR Absorbance for Controlled Delivery of Mixed Anticancer Drugs

Gong

Zhao

Dai

et al. 2017

Chemistry A European J

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“…Taking substantial F atoms off carbon framework of bGF will induce the re‐establishment of π‐conjugated structuration . It is known that the sp 2 ‐hybridized structure of bGF is nearly completely collapsed due to superhigh fluorination degree.…”

Section: Resultsmentioning

confidence: 99%

Nonmainstream Out‐Plane Fluoro‐ and Amino‐Cofunctionalized Graphene for a Striking Electrocatalyst: Programming Substitutive/Reductive Defluorination toward Graphite Fluoride

Zhao

Pan

Kong

et al. 2019

Adv Materials Inter

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It is mostly reported that graphene lattice doped/codoped with heteroatoms (e.g., nitrogen and boron) in an in‐plane fashion exhibits an impressive oxygen reduction reaction (ORR) electrocatalytic efficiency when serving as a metal‐free catalyst, but the cases that graphene sheets functionalized with heteroatoms in an out‐plane scenario are rarely involved. Herein, amino (NH2)‐/fluoro (F)‐cofunctionalized graphene (NH2GF) is rationally designed and synthesized both in out‐plane modes through a programmable substitutive/reductive defluorination toward bulk graphite fluoride using NaNH2. Versatile NH2‐/F‐(co)functionalized graphene products with tunable fluorination and amination are readily yielded and their ORR electrocatalysis is evaluated. Intriguingly, the parameter of NH2/F molar ratio is determinative for their electrocatalytic performances. Consequently, graphene product (roughly formulated in (NH2)7.0C100F2.8, vide infra) dually functionalized with NH2 and F and with an optimized NH2/F factor of 2.5 outperforms others—overmuch in either NH2 only or F only. Encouragingly, (NH2)7.0C100F2.8 even delivers a slightly better electrocatalytic activity than Pt/C catalyst. This finding implies a significant synergistic effect between NH2 and F in boosting graphene electrocatalysis. Apart from fantastic electrocatalytic activity, (NH2)7.0C100F2.8 also exhibits remarkable resistance to crossover effect and exceptional cycling stability.

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“…Better reactivity was achieved by the use of fluorographene (Scheme ). A comprehensive study of reactivity towards different Grignard reagents was made by Otyepka et al . Sofer et al.…”

Section: Synthesis Of Graphene Derivativesmentioning

confidence: 99%

“…The substitution of chlorinated graphene with methylmagnesium bromide was performed by Hossain et al [30] and, for example, with adamantylmagnesium bromide by Sun et al [31] Better reactivityw as achieved by the use of fluorographene (Scheme5). Acomprehensive study of reactivity towards different Grignard reagents was made by Otyepka et al [32] Sofer et al used as eries of Grignardr eagents including simple alkyl chains, vinyl groups, ethynyla nd propargyl group, which contains aterminal triple bond that was used for subsequent functionalization by the use of "click" chemistry. [33] Other approaches for CÀCb ond formation can be based on alkali metal interaction with graphene.…”

Section: Carbon-carbon Bond Formation On Graphene:a Ryl and Alkyl Funmentioning

confidence: 99%

Chemistry of Graphene Derivatives: Synthesis, Applications, and Perspectives

Šturala

Luxa

Pumera

et al. 2018

Chemistry A European J

116

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The chemistry of graphene and its derivatives is one of the hottest topics of current material science research. The derivatisation of graphene is based on various approaches, and to date functionalization with halogens, hydrogen, various functional groups containing oxygen, sulfur, nitrogen, phosphorus, boron, and several other elements have been reported. Most of these functionalizations are based on sp hybridization of carbon atoms in the graphene skeleton, which means the formation of out-of-plane covalent bonds. Several elements were also reported for substitutional modification of graphene, where the carbon atoms are substituted with atoms like nitrogen, boron, and several others. From tens of functional groups, for only two of them were reported full functionalization of graphene skeleton and formation of its stoichiometric counterparts, fluorographene and hydrogenated graphene. The functionalization of graphene is crucial for most of its applications including energy storage and conversion devices, electronic and optic applications, composites, and many others.

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

Cited by 69 publications

References 39 publications

Functionalized Ultrasmall Fluorinated Graphene with High NIR Absorbance for Controlled Delivery of Mixed Anticancer Drugs

Functionalized Ultrasmall Fluorinated Graphene with High NIR Absorbance for Controlled Delivery of Mixed Anticancer Drugs

Nonmainstream Out‐Plane Fluoro‐ and Amino‐Cofunctionalized Graphene for a Striking Electrocatalyst: Programming Substitutive/Reductive Defluorination toward Graphite Fluoride

Chemistry of Graphene Derivatives: Synthesis, Applications, and Perspectives

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