Graphene oxide functionalization via epoxide ring opening in bioconjugation compatible conditions

Ranishenka, Bahdan; Ulashchik, Egor; Tatulchenkov, Maksim; Шарко, О. Л.; Панарин, А.Ю.; Dremova, Nadezhda N.; Shmanai, Vadim V.

doi:10.1016/j.flatc.2021.100235

Cited by 18 publications

(7 citation statements)

References 46 publications

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“…The synthetic procedure was analogous to that described in [ 36 ]. 50 mL of deionized water, 42 mg of sodium bicarbonate, 15 mg sodium citrate, and 450 mg of water-free glucose were added into a round bottom flask and stirred until complete dissolution.…”

Section: Methodsmentioning

confidence: 99%

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Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Ranishenka¹,

Panarin²,

Челнокова³

et al. 2021

Beilstein J. Nanotechnol.

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This work studies the impact of the electrostatic interaction between analyte molecules and silver nanoparticles (Ag NPs) on the intensity of surface-enhanced Raman scattering (SERS). For this, we fabricated nanostructured plasmonic films by immobilization of Ag NPs on glass plates and functionalized them by a set of differently charged hydrophilic thiols (sodium 2-mercaptoethyl sulfonate, mercaptopropionic acid, 2-mercaptoethanol, 2-(dimethylamino)ethanethiol hydrochloride, and thiocholine) to vary the surface charge of the SERS substrate. We used two oppositely charged porphyrins, cationic copper(II) tetrakis(4-N-methylpyridyl) porphine (CuTMpyP4) and anionic copper(II) 5,10,15,20-tetrakis(4-sulfonatophenyl)porphine (CuTSPP4), with equal charge value and similar structure as model analytes to probe the SERS signal. Our results indicate that the SERS spectrum intensity strongly, up to complete signal disappearance, correlates with the surface charge of the substrate, which tends to be negative. Using the data obtained and our model SERS system, we analyzed the modification of the Ag surface by different reagents (lithium chloride, polyethylenimine, polyhexamethylene guanidine, and multicharged metal ions). Finally, all those surface modifications were tested using a negatively charged oligonucleotide labeled with Black Hole Quencher dye. Only the addition of copper ions into the analyte solution yielded a good SERS signal. Considering the strong interaction of copper ions with the oligonucleotide molecules, we suppose that inversion of the analyte charge played a key role in this case, instead of a change of charge of the substrate surface. Changing the charge of analytes could be a promising way to get clear SERS spectra of negatively charged molecules on Ag SERS-active supports.

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Section: Methodsmentioning

confidence: 99%

“…As a silicon support, 5 mm square-shaped polished chips of Sb-doped electrically conductive silicon were used. The modification was performed in a similar way as described in [ 36 ]. The same modification protocol was applied as for glass and the silicon supports.…”

Section: Methodsmentioning

confidence: 99%

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Ranishenka¹,

Panarin²,

Челнокова³

et al. 2021

Beilstein J. Nanotechnol.

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“…The covalent attachment of one epoxy group per nm 2 was achieved via this reaction and most of the functional groups displayed enhanced sustainability after reduction which promoted further azide group functionalization and suppressed the aggregation extent. 186…”

Section: Graphene Graphenoids and (R-)go – 2d Nanocarbonsmentioning

confidence: 99%

Covalent functionalization of 1D and 2D sp²-carbon nanoallotropes – twelve years of progress (2011–2023)

Amjad,

Terzyk,

Boncel

2024

Nanoscale

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“…by ring opening reactions (Figure 2, I) [29] . When thiols are used as nucleophiles, thiol‐epoxide ring opening reaction can occur and some reports can be found in the literature [16,18,29c,30] …”

Section: Classic Chemical Routes To Functionalize Graphene Oxidementioning

confidence: 99%

“…On the other hand, when targeting carboxylic acids, amines commonly are used to produce the respective amide. The kinetics of the reaction is temperature dependent, thus the GO functionalization has been reported in most of the cases by heating [9,28,29c,32] . Hence, the simplest approach consists of performing the reaction by heating while combining GO and the respective amine, and as consequence the amidation proceeds by condensation reaction with a water molecule as a second product.…”

Section: Classic Chemical Routes To Functionalize Graphene Oxidementioning

confidence: 99%

The “How” and “Where” Behind the Functionalization of Graphene Oxide by Thiol‐ene “Click” Chemistry

Piñeiro-García

Semetey

2023

Chemistry A European J

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Graphene oxide (GO) is a 2D nanomaterial with unique chemistry due to the combination of sp2 hybridization and oxygen functional groups (OFGs) even in single layer. OFGs play a fundamental role in the chemical functionalization of GO to produce GO‐based materials for diverse applications. However, traditional strategies that employ epoxides, alcohols, and carboxylic acids suffer from low control and undesirable side reactions, including by‐product formation and GO reduction. Thiol‐ene “click” reaction offers a promising and versatile chemical approach for the alkene functionalization (−C=C−) of GO, providing orthogonality, stereoselectivity, regioselectivity, and high yields while reducing by‐products. This review examines the chemical functionalization of GO via thiol‐ene “click” reactions, providing insights into the underlying reaction mechanisms, including the role of radical or base catalysts in triggering the reaction. We discuss the “how” and “where” the reaction takes place on GO, the strategies to avoid unwanted side reactions, such as GO reduction and by‐product formation. We anticipate that multi‐functionalization of GO via the alkene groups will enhance GO physicochemical properties while preserving its intrinsic chemistry.

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Graphene oxide functionalization via epoxide ring opening in bioconjugation compatible conditions

Cited by 18 publications

References 46 publications

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Covalent functionalization of 1D and 2D sp²-carbon nanoallotropes – twelve years of progress (2011–2023)

The “How” and “Where” Behind the Functionalization of Graphene Oxide by Thiol‐ene “Click” Chemistry

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Graphene oxide functionalization via epoxide ring opening in bioconjugation compatible conditions

Cited by 18 publications

References 46 publications

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu2+ ions

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu2+ ions

Covalent functionalization of 1D and 2D sp2-carbon nanoallotropes – twelve years of progress (2011–2023)

The “How” and “Where” Behind the Functionalization of Graphene Oxide by Thiol‐ene “Click” Chemistry

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Product

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Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Modification of a SERS-active Ag surface to promote adsorption of charged analytes: effect of Cu²⁺ ions

Covalent functionalization of 1D and 2D sp²-carbon nanoallotropes – twelve years of progress (2011–2023)