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REVIEW 4 major objections 7 minor 63 references

Surface Grafting of Graphene Flakes with Fluorescent Dyes: A Tailored Functionalization Approach

T0 review · 4 major / 7 minor · reviewed 2026-08-15 · deepseek-v4-flash

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Pith's one-line read The paper reports a three-step covalent route that attaches fluorescent Atto dyes to low-defect graphene flakes by 1,3-dipolar cycloaddition of a Boc-protected ylide, followed by deprotection and NHS-ester coupling.

desk verdict A useful linker platform for dye-labeling low-defect graphene, but the covalent amide bond is inferred rather than directly shown. read the letter →

arxiv 2505.03365 v1 pith:EY6TSHLY submitted 2025-05-06 cond-mat.mtrl-sci

Ylea Vlamidis , Carmela Marinelli , Aldo Moscardini , Paolo Faraci , Stefan Heun , Stefano Veronesi This is my paper · ORCID
classification cond-mat.mtrl-sci
keywords graphenefunctionalization13-dipolarcycloadditionazomethineylideBocprotectinggroupNHSestercouplingfluorescentdyesRamanspectroscopyconfocalfluorescencemicroscopy
verification ladder T0 review T1 audit T2 compute T3 formal

The pith

A machine-rendered reading of the paper's core claim, the machinery that carries it, and where it could break.

The reading

The paper claims that low-defect graphene flakes can be covalently labeled with fluorescent dyes through a three-step sequence: 1,3-dipolar cycloaddition of a custom Boc-protected azomethine ylide, acid cleavage of the Boc group, and NHS-ester coupling of an Atto dye to the exposed amine. The authors argue that the reaction is selective for the flakes' sparse defects and edges, so the graphene lattice is not heavily damaged, and that the dye is genuinely attached through the linker rather than merely adsorbed. They support this with Raman spectra showing the D-to-G intensity ratio dropping from about 0.11 to 0.022, photoluminescence from three different Atto dyes, confocal fluorescence images, and control samples that show no fluorescence when the linker or the cycloaddition step is omitted. The significance, if the claim holds, is a general platform for attaching molecules, quantum dots, or nanoparticles to nearly pristine graphene without destroying its useful properties.

What carries the argument

The load-bearing object is the custom-synthesized Boc-protected azomethine ylide: a mono-Boc-protected diamine derivative that undergoes 1,3-dipolar cycloaddition with graphene to form a pyrrolidine ring, leaving a protected amine pointing away from the surface. Boc cleavage exposes the primary amine, which is then coupled to the NHS ester of the dye through an amide bond. The three-step scheme—ylide grafting, deprotection, NHS coupling—is what carries the argument, because each step is independently checkable by Raman, FT-IR, photoluminescence, or fluorescence-lifetime data.

What would settle it

A decisive experiment is to track the same flakes by Raman mapping before and after functionalization and to measure the wash supernatant: if the I(D)/I(G) drop is caused by selective removal of defective flakes, the missing D-band signal will appear in the removed material, whereas if grafting is the cause, the same flakes will show the lower ratio while still present. A complementary check is direct XPS measurement of nitrogen or dye loading on the final flakes, which would verify the assumed one-linker-per-170-carbons density rather than borrowing it from earlier work.

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Extended reading notes

Core claim

The central claim is that 1,3-dipolar cycloaddition—the same azomethine-ylide chemistry previously applied to carbon nanotubes—works on few-layer graphene flakes that have very few lattice defects, and that a Boc-protected amine built into the ylide leaves a handle for later conjugation. After grafting, acid deprotection exposes a primary amine, and an NHS-ester derivative of Atto 425, 465, or 633 forms an amide bond to that amine. The Raman signature of the functionalized flakes shows the D band intensity decreasing relative to the G band, which the authors interpret as the ylide saturating the reactive defect and edge sites; the 2D band is essentially unchanged, indicating that basal-plane order is preserved. Photoluminescence and confocal imaging show emission at the dyes' characteristic wavelengths, absent in controls lacking the linker or the cycloaddition step, and time-resolved fluorescence of the bound dyes becomes double-exponential, consistent with energy transfer from dye to graphene. The paper also states that the grafting density is about one linker per 170 carbon atoms, taken from a prior study using the same reaction, and that the labeled flakes remain fluorescent after more than a year of storage.

Load-bearing premise

The argument hinges on interpreting the drop in the Raman I(D)/I(G) ratio from about 0.11 to 0.022 as the ylide molecules saturating defects and edges; if defective flakes were instead removed during washing, or if laser exposure reorganized the lattice, the covalent-grafting conclusion would not follow.

Editorial extensions

If this is right

  • Because the dye is attached through a primary amine, any NHS-ester-functionalized cargo—peptides, proteins, quantum dots, or nanoparticles—could be anchored to low-defect graphene by the same three-step sequence.
  • Raman and fluorescence together let a user locate reactive sites: the D-band drop tracks defect and edge saturation, while fluorescence images show where the dye actually landed.
  • The minimal change in the 2D Raman band suggests the graphene lattice remains largely intact, so functionalized flakes should retain more of graphene's conductivity and mechanical properties than radical-based functionalization would allow.
  • The method works with three dyes spanning blue to red emission, so multicolor labeling of single flakes is within reach.
  • Samples stored in the dark stayed fluorescent for over a year, which makes the route practical for real device or assay timelines.

Reading between the lines

Editorial extensions of the paper, not claims the author makes directly.

  • Not pursued in the paper: if grafting density tracks reactive sites, the confocal fluorescence intensity per flake area could be calibrated against Raman defect counts and become a quick, nondestructive assay for defect density in batch-produced graphene.
  • A testable extension the paper leaves implicit is to vary linker length and measure the fluorescence-lifetime components: the observed double-exponential decay suggests distance-dependent energy transfer to graphene, so FLIM could serve as a ruler for dye–graphene separation.
  • I infer from the control experiments that fluorescence appears only where a free amine is present, so the method could be spatially patterned by deprotecting or activating selected regions before dye coupling.
  • If the one-per-170-carbons density carries over, adjacent linkers sit roughly 2 nm apart; at that spacing, energy transfer between neighboring dyes of different colors should be detectable, offering a way to test the assumed density without XPS.
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Editorial analysis

A structured set of objections, weighed in public.

Desk editor's note, referee report, and a circularity audit.

Referee Report

4 major / 7 minor

Summary. The manuscript reports a three-step route for the covalent functionalization of low-defect, few-layer graphene flakes with three Atto fluorophores. Step I is a 1,3-dipolar cycloaddition of a custom Boc-protected azomethine ylide (formed in situ from a mono-Boc hexamethylenediamine-derived linker and 3,4-dihydroxybenzaldehyde), step II is Boc deprotection with phosphoric acid, and step III is coupling of Atto 425/465/633 NHS esters to the surface amines. Functionalization is argued from a decrease in the Raman I(D)/I(G) ratio (from about 0.11 to 0.022, Section 3.2), from dye-specific photoluminescence that is absent in control samples, from confocal fluorescence imaging, and from FLIM decays that become double-exponential after grafting. The authors conclude that the dyes are covalently attached via an amide linkage and that the platform can anchor other molecules such as quantum dots and nanoparticles.

Significance. If the covalent-attachment claim holds, the paper provides a useful proof of concept: a Boc-protected ylide strategy that decouples cycloaddition from payload attachment, demonstrated consistently with three spectrally distinct dyes on low-defect graphene flakes. The strengths are the two control experiments (dye on pristine graphene, linker without dye), the statistical Raman analysis over 75 spectra, the wavelength-consistent emission for all three dyes, and the reported one-year stability of the labeled flakes. The significance is incremental rather than transformative; the advance is a chemical-route demonstration, and the central claim currently rests on circumstantial rather than direct evidence of the amide bond. The manuscript is appropriate in scope for a materials-chemistry journal and is publishable if the covalent-linkage evidence is strengthened.

major comments (4)
  1. [Section 3.3, Figure 4b] The two control experiments rule out dye physisorption on pristine graphene and intrinsic fluorescence of the linker-graphene system, but neither control addresses the surface that actually exists after step II. After Boc deprotection the flakes carry free amine groups and an organic layer whose surface chemistry differs from pristine graphene, and dye molecules could adsorb on or become trapped in this layer even without forming an amide bond; the DMSO/acetonitrile/acetone rinses described in Section 2.3 may not remove such species. The final product is not characterized by any direct chemical signature of the amide bond: the FT-IR data in SI Figure S2 are taken after deprotection and before dye coupling, and no XPS, Raman, or mass-spectrometric evidence for the dye-linker linkage is presented. The abstract's statement that the dyes are 'covalently linked' therefore overstates what the data establish. Additional evidence is needed, for example XPS N 1s and C 1s analysis, or a control in which the deprotected linker-functionalized flakes are exposed to an Atto dye lacking the NHS ester, or to the NHS-ester dye under non-coupling conditions.
  2. [Section 3.2, Figure 3a] The decrease in I(D)/I(G) from about 0.11 to 0.022 is interpreted as grafting at defect sites and edge saturation, but alternative explanations are not excluded. The washing protocol (centrifugation at 13,000 rpm with resuspension, Section 2.3) can size-select or remove the most defective flakes, and the 75 spectra were acquired from different flakes before and after functionalization rather than from the same flakes in a paired measurement. The interpretation also sits in tension with the functionalization density assumed later in the same section: one ylide per about 170 carbon atoms would introduce roughly 1% sp3 carbon, which standard defect-activated Raman models (refs. [49,50]) would be expected to increase rather than reduce the D band. The authors should report paired same-flake spectra or a wash-only control, and should discuss quantitatively how edge passivation can outweigh the sp3 defects introduced by the claimed grafting density.
  3. [Section 3.2, 'The degree of functionalization...'] The quantitative claim of one ylide per about 170 carbon atoms is borrowed from ref. [31], where a 'closely similar' ylide was used, and is not measured in this work. The linker molecule, the reaction conditions (120 h at 150 °C with daily reagent addition), and the flake source are specific to the present study, so the transferred value carries substantial uncertainty. If a functionalization density is stated, it should be measured on the present samples (e.g., by XPS, as in ref. [31]); otherwise the statement should be reworded as an unverified assumption and the quantitative discussion adjusted accordingly.
  4. [Section 3.3, Figure 4d and Table S1] The double-exponential decays (tau1 about 0.5-0.8 ns, tau2 about 2.6-2.9 ns) are attributed to rapid energy transfer to graphene plus the intrinsic dye decay. This is plausible, but it does not discriminate between a covalently bound dye and a dye merely held in proximity to the graphene surface, since both would experience graphene-induced energy transfer; the conclusion that attachment to graphene alters the fluorescence dynamics does not by itself support the covalent-linkage claim. The fit model, amplitudes, and goodness-of-fit are not reported, and alternative interpretations (e.g., a distribution of dye-graphene distances or dye aggregation) are not discussed. These data should be presented as consistent with, rather than evidence for, covalent binding.
minor comments (7)
  1. [Section 2.1] The abbreviation 'DFM' for N,N-dimethylformamide is a typo for DMF, which is used correctly elsewhere.
  2. [Section 2.2] The text uses 'trimethylamine' where the reagent list and the reaction scheme require triethylamine; this should be corrected for consistency.
  3. [Reference [32]] The citation lists J. Mater. Chem. C with volume and page numbers but a preprint DOI (10.2139/ssrn.4039980); this should be reconciled with the published version.
  4. [SI Figure S2] Assigning the band at 1730 cm-1 to an amide C=O stretch in the product of the deprotection step is chemically questionable, since no amide is expected after Boc cleavage; a residual carbamate or other carbonyl assignment should be considered, and the confirmation of deprotection would be better supported by free-amine N-H bands.
  5. [Section 2.4] The laser irradiation is quoted in units of mJ per square micrometer as 'power'; this is a fluence, and the actual power or pulse parameters should be stated.
  6. [Section 3.3 and SI Figure S5] The text claims a 'uniform derivatization of both the edges and the basal plane' while also attributing fluorescence intensity variations to the 'random distribution of defects'; these statements should be reconciled.
  7. [SI Figure S3 caption] 'Atto 465 NSH' should read 'Atto 465 NHS'.

Circularity Check

0 steps flagged · score 0.0 of 10

No circularity found: the central dye-attachment claim rests on new fluorescence, confocal, and FLIM data with controls, not on a reduction of the inputs.

full rationale

The claimed derivation chain is experimental: synthesize a Boc-protected linker (UHPLC-MS), graft it to graphene by 1,3-dipolar cycloaddition (Raman and prior XPS/DFT work), deprotect the amine (FT-IR), and attach NHS-ester dyes (PL, confocal, FLIM). No quantity called a prediction is obtained by construction from the data used to define it. The one ylide per ~170 carbon atoms functionalization density is explicitly imported from prior self-cited work as an assumption ('therefore, it is reasonable to assume a comparable functionalization rate'), not fitted or renamed as a new result, and it does not feed back into the fluorescence evidence for dye attachment. The self-citations [31,32] concern the same cycloaddition chemistry and are externally evidenced (XPS, EDX, DFT); they are background support rather than a forced derivation of the new dye-labeling claim. The new controls (linker without dye, pristine graphene incubated with dye) independently show no fluorescence, which supports the attachment interpretation. The absence of a direct amide-bond signature is a real evidentiary limitation about covalent bonding, but it is not circularity, because the paper's positive fluorescence evidence is not equivalent to its own inputs.

Assumptions & free parameters 2 free parameters · 5 assumptions · 0 invented entities

The central claim rests on the known 1,3-DC mechanism and reaction parameters from the authors' prior work, on the interpretation of Raman changes as defect-site grafting, and on the assumption that the functionalization density matches an earlier XPS estimate. The fluorescence controls are independent evidence, but the density and the defect-targeting interpretation are not directly measured here.

free parameters (2)
  • FLIM fast lifetime tau1 = 0.5 to 0.8 ns depending on dye
    Double-exponential fit to fluorescence decay of dye-labeled graphene; used to interpret energy transfer to graphene, not to establish successful attachment.
  • FLIM slow lifetime tau2 = 2.6 to 2.9 ns depending on dye
    Second lifetime component in the same double-exponential fit, attributed to intrinsic dye decay.
assumptions (5)
  • domain assumption 1,3-dipolar cycloaddition of azomethine ylide occurs on graphene flakes as described in refs [31] and [32].
    The paper uses the same reaction mechanism and parameters as its own prior work; the success of grafting is inferred from Raman changes and prior XPS.
  • domain assumption The decrease in I(D)/I(G) after functionalization is due to grafting at defects and edge saturation.
    Section 3.2; alternative explanations such as washing away defective flakes or laser-induced changes are not rigorously excluded.
  • domain assumption Functionalization density is comparable to that in ref [31], about one ylide per 170 carbon atoms.
    Section 3.2; stated as reasonable to assume because the ylide and conditions are similar, but not measured in this work.
  • domain assumption FT-IR band assignments indicate complete Boc cleavage.
    Supporting Information Figure S2; band assignments are qualitative and no quantitative analysis is given.
  • domain assumption Fluorescence signal from dye-labeled graphene is due to covalent attachment, not physisorption.
    Supported by controls (dye without linker shows no signal), but the possibility of residual non-covalent interactions is not fully excluded.

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Cite this review

Pith. "Pith review of Surface Grafting of Graphene Flakes with Fluorescent Dyes: A Tailored Functionalization Approach." pith.science (2026). https://pith.science/paper/EY6TSHLY

@misc{pith2026250503365,
  author       = {Pith},
  title        = {Pith review of: Surface Grafting of Graphene Flakes with Fluorescent Dyes: A Tailored Functionalization Approach},
  year         = {2026},
  howpublished = {\url{https://pith.science/paper/EY6TSHLY}},
  note         = {Machine review of arXiv:2505.03365}
}
read the original abstract

The controlled functionalization of graphene is critical for tuning and enhancing its properties, thereby expanding its potential applications. Covalent functionalization offers a deeper tuning of the geometric and electronic structure of graphene compared to non-covalent methods; however, the existing techniques involve side reactions and spatially uncontrolled functionalization, pushing research toward more selective and controlled methods. A promising approach is 1,3-dipolar cycloaddition, successfully utilized with carbon nanotubes. In the present work, this method has been extended to graphene flakes with low defect concentration. A key innovation is the use of a custom-synthesized ylide with a protected amine group (Boc), facilitating subsequent attachment of functional molecules. Indeed, after Boc cleavage, fluorescent dyes (Atto 425, 465, and 633) were covalently linked via NHS ester derivatization. This approach represents a highly selective method of minimizing structural damage. Successful functionalization was demonstrated by Raman spectroscopy, photoluminescence spectroscopy, and confocal microscopy, confirming the effectiveness of the method. This novel approach offers a versatile platform, enabling its use in biological imaging, sensing, and advanced nanodevices. The method paves the way for the development of sensors and devices capable of anchoring a wide range of molecules, including quantum dots and nanoparticles. Therefore, it represents a significant advancement in graphene-based technologies.

Figures

Figures reproduced from arXiv: 2505.03365 by the authors.

Figure 1
Figure 1. Schematic flowchart describing the multi-step functionalization of graphene flakes with fluorescent molecules [PITH_FULL_IMAGE:figures/full_fig_p004_1.png] view at source ↗
Figure 2
Figure 2. (a) AFM topography with (b) height profile along the white line indicated in (a). (c,d) SEM images at different magnification of the graphene flakes drop-cast on Si/SiO2 from a chloroform suspension. The Raman spectrum of functionalized graphene (Figure 3a) shows clearly a decreased intensity of the D peak compared to the pristine sample. The defect density can be assessed by the peak intensity ratio between the D b… view at source ↗
Figure 3
Figure 3. (a) Representative normalized Raman spectra acquired from pristine and linker-functionalized graphene flakes on Si/SiO2. The inset shows a histogram of the I(D)/I(G) peak intensity ratio extracted from the Raman spectra (statistical analysis of 75 spectra acquired from different flakes). Histogram colors are used according to the colors of the curves shown in panel (a). (b) Optical bright field microscopy image (100… view at source ↗
Figures from the paper (2 more)
Figure 4
Figure 4. Figure 4: (a) PL spectra acquired at 473 nm excitation for Atto 465-labeled graphene flakes and the pristine sample. (b) PL spectra of functionalized graphene flakes (black curve) and control samples: graphene flakes functionalized with only the linker molecule (red line) and gr…
Figure 5
Figure 5. Figure 5: Fluorescence spectra of graphene flakes functionalized with (a) Atto 425 NHS and (b) Atto 633 NHS compared with the blank signal. The data were acquired with a confocal microscope under excitation at 440 nm and 640 nm, respectively. The insets show representative fluor…

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Works this paper leans on

63 extracted references · 58 canonical work pages

  1. [31]

    Covalent organic functionalization of graphene nanosheets and reduced graphene oxide via1,3-dipolar cycloaddition of azomethine ylide

    Basta, L.; Moscardini, A.; Fabbri, F.; Bellucci, L.; Tozzini, V.; Rubini, S.; Griesi, A.; Gemmi, M.; Heun, S.; Veronesi, S. Covalent organic functionalization of graphene nanosheets and reduced graphene oxide via1,3-dipolar cycloaddition of azomethine ylide. Nanoscale Adv. 2021, 3, 5841–5852. https://doi.org/10.1039/d1na00335f

    work page doi:10.1039/d1na00335f 2021

  2. [1]

    Electric Field Effect in Atomically Thin Carbon Films

    Novoselov, K.S.; Geim, A.K.; Morozov, S.V.; Jiang, D.; Zhang, Y.; Dubonos, S.V.; Grigorieva, I.V.; Firsov, A.A. Electric Field Effect in Atomically Thin Carbon Films. Science 2004, 306, 666–669. https://doi.org/10.1126/science.1102896

    doi:10.1126/science.1102896 2004

  3. [2]

    Production, properties and potential of graphene

    Soldano, C.; Mahmood, A.; Dujardin, E. Production, properties and potential of graphene. Carbon 2010, 48, 2127–2150. https://doi.org/10.1016/j.carbon.2010.01.058

    work page doi:10.1016/j.carbon.2010.01.058 2010

  4. [3]

    Electronic properties of graphene

    Novoselov, K.S.; Morozov, S.V.; Mohinddin, T.M.G.; Ponomarenko, L.A.; Elias, D.C.; Yang, R.; Barbolina, I.I.; Blake, P.; Booth, T.J.; Jiang, D.; et al. Electronic properties of graphene. Phys. Status Solidi Basic Res . 2007, 244 , 4106–4111. https://doi.org/10.1002/pssb.200776208

    work page doi:10.1002/pssb.200776208 2007

  5. [4]

    Recent Progress in Graphene/Polymer Nanocomposites

    Sun, X.; Huang, C.; Wang, L.; Liang, L.; Cheng, Y.; Fei, W.; Li, Y. Recent Progress in Graphene/Polymer Nanocomposites. Adv. Mater . 2021, 33 , 2001105. https://doi.org/10.1002/adma.202001105

    work page doi:10.1002/adma.202001105 2021

  6. [5]

    Graphene-based materials for supercapacitor electrodes—A review

    Ke, Q.; Wang, J. Graphene-based materials for supercapacitor electrodes—A review. J. Mater. 2016, 2, 37–54. https://doi.org/10.1016/j.jmat.2016.01.001

    work page doi:10.1016/j.jmat.2016.01.001 2016

  7. [6]

    Graphene-based nanomaterials for drug delivery and tissue engineering

    Goenka, S.; Sant, V.; Sant, S. Graphene-based nanomaterials for drug delivery and tissue engineering. J. Control. Release 2014, 173 , 75–88. https://doi.org/10.1016/j.jconrel.2013.10.017

    work page doi:10.1016/j.jconrel.2013.10.017 2014

  8. [7]

    Transparent, conductive graphene electrodes for dye-sensitized solar cells

    Wang, X.; Zhi, L.; Müllen, K. Transparent, conductive graphene electrodes for dye-sensitized solar cells. Nano Lett. 2008, 8, 323–327. https://doi.org/10.1021/nl072838r. 16

    work page doi:10.1021/nl072838r 2008

Show all 63 references
  1. [8]

    Flexible organic memory devices with multilayer graphene electrodes

    Ji, Y.; Lee, S.; Cho, B.; Song, S.; Lee, T. Flexible organic memory devices with multilayer graphene electrodes. ACS Nano 2011, 5, 5995–6000. https://doi.org/10.1021/nn201770s

    2011 doi

  2. [9]

    A Flexible, Transparent Chemosensor Integrating an Inkjet-Printed Organic Field-Effect Transistor and a Non-Covalently Functionalized Graphene Electrode

    Lai, S.; Vlamidis, Y.; Mishra, N.; Cosseddu, P.; Mišeikis, V.; Ricci, P.C.; Voliani, V.; Coletti, C.; Bonfiglio, A. A Flexible, Transparent Chemosensor Integrating an Inkjet-Printed Organic Field-Effect Transistor and a Non-Covalently Functionalized Graphene Electrode. Adv. Ma...

    2021 doi

  3. [10]

    Probing the electrochemical properties of graphene nanosheets for biosensing applications

    Alwarappan, S.; Erdem, A.; Liu, C.; Li, C.Z. Probing the electrochemical properties of graphene nanosheets for biosensing applications. J. Phys. Chem. C 2009, 113, 8853–8857. https://doi.org/10.1021/jp9010313

    2009 doi

  4. [11]

    Manipulating the electronic and chemical properties of graphene via molecular functionalization

    Mao, H.Y.; Lu, Y.H.; Lin, J.D.; Zhong, S.; Wee, A.T.S.; Chen, W. Manipulating the electronic and chemical properties of graphene via molecular functionalization. Prog. Surf. Sci. 2013, 88, 132–159. https://doi.org/10.1016/j.progsurf.2013.02.001

    2013 doi

  5. [12]

    Controlling covalent chemistry on graphene oxide

    Guo, S.; Garaj, S.; Bianco, A.; Ménard-Moyon, C. Controlling covalent chemistry on graphene oxide. Nat. Rev. Phys. 2022, 4, 247–262. https://doi.org/10.1038/s42254-022- 00422-w

    2022 doi

  6. [13]

    Guiding graphene derivatization for covalent immobilization of aptamers

    Rabchinskii, M.K.; Ryzhkov, S.A.; Besedina, N.A.; Brzhezinskaya, M.; Malkov, M.N.; Stolyarova, D.Y.; Arutyunyan, A.F.; Struchkov, N.S.; Saveliev, S.D.; Diankin, I.D.; et al. Guiding graphene derivatization for covalent immobilization of aptamers. Carbon 2022, 196, 264–279. htt...

    2022 doi

  7. [14]

    Toward On-Chip Multisensor Arrays for Selective Methanol and Ethanol Detection at Room Temperature: Capitalizing the Graphene Carbonylation

    Rabchinskii, M.K.; Sysoev, V.V.; Varezhnikov, A.S.; Solomatin, M.A.; Struchkov, N.S.; Stolyarova, D.Y.; Ryzhkov, S.A.; Antonov, G.A.; Gabrelian, V.S.; Cherviakova, P.D.; et al. Toward On-Chip Multisensor Arrays for Selective Methanol and Ethanol Detection at Room Temperature: ...

    2023 doi

  8. [15]

    An Overview of Functionalized Graphene Nanomaterials for Advanced Applications

    Maio, A.; Pibiri, I.; Morreale, M.; La Mantia, F.P.; Scaffaro, R. An Overview of Functionalized Graphene Nanomaterials for Advanced Applications. Nanomaterials 2021, 11,

    2021

  9. [16]

    Chemical Functionalization of Graphene with Defects

    Boukhvalov, D.W.; Katsnelson, M.I. Chemical Functionalization of Graphene with Defects. Nano Lett. 2008, 8, 4373–4379. https://doi.org/10.1021/nl802234n

    2008 doi

  10. [17]

    Graphene and functionalized graphene: Extraordinary prospects for nanobiocomposite materials

    Ioniţă, M.; Vlăsceanu, G.M.; Watzlawek, A.A.; Voicu, S.I.; Burns, J.S.; Iovu, H. Graphene and functionalized graphene: Extraordinary prospects for nanobiocomposite materials. Compos. Part B Eng. 2017, 121, 34–57. https://doi.org/10.1016/j.compositesb.2017.03.031

    2017 doi

  11. [18]

    Water-soluble graphene covalently functionalized by biocompatible poly-L-lysine

    Shan, C.; Yang, H.; Han, D.; Zhang, Q.; Ivaska, A.; Niu, L. Water-soluble graphene covalently functionalized by biocompatible poly-L-lysine. Langmuir 2009, 25 , 12030–12033. https://doi.org/10.1021/la903265p

    2009 doi

  12. [19]

    Multifunctional organically modified graphene with super-hydrophobicity

    Hu, H.; Allan, C.C.K.; Li, J.; Kong, Y.; Wang, X.; Xin, J.H.; Hu, H. Multifunctional organically modified graphene with super-hydrophobicity. Nano Res. 2014, 7, 418–433. https://doi.org/10.1007/s12274-014-0408-0

    2014 doi

  13. [20]

    The chemistry of graphene

    Loh, K.P.; Bao, Q.; Ang, P.K.; Yang, J. The chemistry of graphene. J. Mater. Chem. 2010, 20, 2277–2289. https://doi.org/10.1039/b920539j

    2010 doi

  14. [21]

    Functionalization of Graphene and Applications of the Derivatives

    Yang, G.-h.; Bao, D.-d., Liu, H.; Zhang, D.-q.; Wang, N.; Li, H.-t. Functionalization of Graphene and Applications of the Derivatives. J. Inorg. Organomet. Polym. Mater. 2017, 27, 1129–1141. https://doi.org/10.1007/s10904-017-0597-6

    2017 doi

  15. [22]

    The Covalent Functionalization of Graphene on Substrates

    Criado, A.; Melchionna, M.; Marchesan, S.; Prato, M. The Covalent Functionalization of Graphene on Substrates. Angew. Chem. Int. Ed . 2015, 54 , 10734–10750. https://doi.org/10.1002/anie.201501473. 17

    2015 doi

  16. [23]

    The Covalent Functionalization of Surface-Supported Graphene: An Update

    Wetzl, C.; Silvestri, A.; Garrido, M.; Hou, H.L.; Criado, A.; Prato, M. The Covalent Functionalization of Surface-Supported Graphene: An Update. Angew. Chem. Int. Ed. 2023, 62, e202212857. https://doi.org/10.1002/anie.202212857

    2023 doi

  17. [24]

    Covalent functionalization of epitaxial graphene by azidotrimethylsilane

    Choi, J.; Kim, K.J.; Kim, B.; Lee, H.; Kim, S. Covalent functionalization of epitaxial graphene by azidotrimethylsilane. J. Phys. Chem. C 2009, 113 , 9433–9435. https://doi.org/10.1021/jp9010444

    2009 doi

  18. [25]

    N-Heterocyclic Carbene–Graphene Nanotransistor Based on Covalent Bond for Ultrastable Biosensors

    Kim, K.H.; Seo, S.E.; Park, S.J.; Kim, J.; Park, C.S.; Le, T.H.; Lee, C.S.; Kim, Y.K.; Kim, H.Y.; Jun, S.; et al. N-Heterocyclic Carbene–Graphene Nanotransistor Based on Covalent Bond for Ultrastable Biosensors. Adv. Funct. Mater . 2024, 34 , 2310377. https://doi.org/10.1002/a...

    2024 doi

  19. [26]

    Microwave- induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions

    Sulleiro, M.V.; Quiroga, S.; Peña, D.; Pérez, D.; Guitián, E.; Criado, A.; Prato, M. Microwave- induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions. Chem. Commun. 2018, 54, 2086–2089. https://doi.org/10.1039/c7cc08676h

    2018 doi

  20. [27]

    Organic functionalisation of graphenes

    Georgakilas, V.; Bourlinos, A.B.; Zboril, R.; Steriotis, T.A.; Dallas, P.; Stubos, A.K.; Trapalis, C. Organic functionalisation of graphenes. Chem. Commun. 2010, 46, 1766–1768. https://doi.org/10.1039/b922081j

    2010 doi

  21. [28]

    1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: Synthesis of derivatives of 2′,5′-dihydro-1′H- pyrrolo[3′,4′:1,2][60]fullerene 1

    Wu, S.; Sun, W.; Zhang, D.; Shu, L.; Wu, H.; Xu, J.; Lao, X. 1,3-Dipolar cycloaddition of several azomethine ylides to [60]fullerene: Synthesis of derivatives of 2′,5′-dihydro-1′H- pyrrolo[3′,4′:1,2][60]fullerene 1. J. Chem. Soc., Perkin Trans. 1998, 1 , 1733–1738. https://doi...

    1998 doi

  22. [29]

    Fluorescent single-walled carbon nanotubes following the 1,3- dipolar cycloaddition of pyridinium ylides

    Bayazit, M.K.; Coleman, K.S. Fluorescent single-walled carbon nanotubes following the 1,3- dipolar cycloaddition of pyridinium ylides. J. Am. Chem. Soc. 2009, 131, 10670–10676. https://doi.org/10.1021/ja903712f

    2009 doi

  23. [30]

    An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions

    Filippone, S.; Maroto, E.E.; Martín-Domenech, Á.; Suarez, M.; Martín, N. An efficient approach to chiral fullerene derivatives by catalytic enantioselective 1,3-dipolar cycloadditions. Nat. Chem. 2009, 1, 578–582. https://doi.org/10.1038/nchem.361

    2009 doi

  24. [32]

    Deterministic Covalent Organic Functionalization of Monolayer Graphene with 1,3- Dipolar Cycloaddition Via High Resolution Surface Engineering

    Basta, L.; Bianco, F.; Moscardini, A.; Fabbri, F.; Bellucci, L.; Tozzini, V.; Heun, S.; Veronesi, S. Deterministic Covalent Organic Functionalization of Monolayer Graphene with 1,3- Dipolar Cycloaddition Via High Resolution Surface Engineering. J. Mater. Chem. C 2022, 11, 2630...

    2022 doi

  25. [33]

    A multicolor fluorescence in situ hybridization approach using an extended set of fluorophores to visualize microorganisms

    Lukumbuzya, M.; Schmid, M.; Pjevac, P.; Daims, H. A multicolor fluorescence in situ hybridization approach using an extended set of fluorophores to visualize microorganisms. Front. Microbiol. 2019, 10, 1383. https://doi.org/10.3389/fmicb.2019.01383

    2019

  26. [34]

    Atto 465 Derivative Is a Nuclear Stain with Unique Excitation and Emission Spectra Useful for Multiplex Immunofluorescence Histochemistry

    Dodge, J.T.; Doyle, A.D.; Costa-da-Silva, A.C.; Hogden, C.T.; Mezey, E.; Mays, J.W. Atto 465 Derivative Is a Nuclear Stain with Unique Excitation and Emission Spectra Useful for Multiplex Immunofluorescence Histochemistry. J. Histochem. Cytochem. 2022, 70, 211–223. https://doi...

    2022 doi

  27. [35]

    Determining the In-Plane Orientation and Binding Mode of Single Fluorescent Dyes in DNA Origami Structures

    Hübner, K.; Joshi, H.; Aksimentiev, A.; Stefani, F.D.; Tinnefeld, P.; Acuna, G.P. Determining the In-Plane Orientation and Binding Mode of Single Fluorescent Dyes in DNA Origami Structures. ACS Nano 2021, 15, 5109–5117. https://doi.org/10.1021/acsnano.0c10259. 18

    2021 doi

  28. [36]

    Carbon Nanomaterial Fluorescent Probes and Their Biological Applications

    Krasley, A.T.; Li, E.; Galeana, J.M.; Bulumulla, C.; Beyene, A.G.; Demirer, G.S. Carbon Nanomaterial Fluorescent Probes and Their Biological Applications. Chem. Rev. 2024, 124, 3085–3185. https://doi.org/10.1021/acs.chemrev.3c00581

    2024 doi

  29. [37]

    Intracellular imaging with a graphene-based fluorescent probe

    Peng, C.; Hu, W.; Zhou, Y.; Fan, C.; Huang, Q. Intracellular imaging with a graphene-based fluorescent probe. Small 2010, 6, 1686–1692. https://doi.org/10.1002/smll.201000560

    2010 doi

  30. [38]

    Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters

    Halbig, C.E.; Lasch, R.; Krüll, J.; Pirzer, A.S.; Wang, Z.; Kirchhof, J.N.; Bolotin, K.I.; Heinrich, M.R.; Eigler, S. Selective Functionalization of Graphene at Defect-Activated Sites by Arylazocarboxylic tert-Butyl Esters. Angew. Chem. Int. Ed. 2019, 58, 3599–3603. https://do...

    2019 doi

  31. [39]

    Succinimidyl ester surface chemistry: Implications of the competition between aminolysis and hydrolysis on covalent protein immobilization

    Lim, C.Y.; Owens, N.A.; Wampler, R.D.; Ying, Y.; Granger, J.H.; Porter, M.D.; Takahashi, M.; Shimazu, K. Succinimidyl ester surface chemistry: Implications of the competition between aminolysis and hydrolysis on covalent protein immobilization. Langmuir 2014, 30, 12868–12878. ...

    2014 doi

  32. [40]

    Surface functionalization of graphene-based materials: Biological behavior, toxicology, and safe-by-design aspects

    Guo, Z.; Chakraborty, S.; Monikh, F.A.; Varsou, D.-D.; Chetwynd, A.J.; Afantitis, A.; Lynch, I.; Zhang, P. Surface functionalization of graphene-based materials: Biological behavior, toxicology, and safe-by-design aspects. Adv. Biol. 2021, 5 , 2100637. https://doi.org/10.1002/...

    2021 doi

  33. [41]

    Amino Acid-Protecting Groups

    Isidro-Llobet, A.; Álvarez, M.; Albericio, F. Amino Acid-Protecting Groups. Chem. Rev. 2009, 109, 2455–2504. https://doi.org/10.1021/cr800323s

    2009 doi

  34. [42]

    Versatile functionalization of 3,5- diamino-4-nitropyrazole for promising insensitive energetic compounds

    Tang, Y.; Ma, J.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Versatile functionalization of 3,5- diamino-4-nitropyrazole for promising insensitive energetic compounds. Dalt. Trans. 2019, 48, 14490–14496. https://doi.org/10.1039/c9dt03138c

    2019 doi

  35. [43]

    Zwitterionic Halido Cyclopentadienone Iron Complexes and Their Catalytic Performance in Hydrogenation Reactions

    Bütikofer, A.; Chen, P. Zwitterionic Halido Cyclopentadienone Iron Complexes and Their Catalytic Performance in Hydrogenation Reactions. Inorg. Chem. 2023, 62, 4188–4196. https://doi.org/10.1021/acs.inorgchem.2c04298

    2023 doi

  36. [44]

    Selective mono-BOC protection of diamines

    Lee, D.W.; Ha, H.J.; Lee, W.K. Selective mono-BOC protection of diamines. Synth. Commun. 2007, 37, 737–742. https://doi.org/10.1080/00397910601131403

    2007 doi

  37. [45]

    Mild deprotection of the: N-tert- butyloxycarbonyl (N-Boc) group using oxalyl chloride

    George, N.; Ofori, S.; Parkin, S.; Awuah, S.G. Mild deprotection of the: N-tert- butyloxycarbonyl (N-Boc) group using oxalyl chloride. RSC Adv. 2020, 10, 24017–24026. https://doi.org/10.1039/d0ra04110f

    2020 doi

  38. [46]

    Amidation and esterification of carboxylic acids with amines and phenols by N,N′-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water

    Fattahi, N.; Ayubi, M.; Ramazani, A. Amidation and esterification of carboxylic acids with amines and phenols by N,N′-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water. Tetrahedron 2018, 74 , 4351–4356. https://doi.org/10.1016/j.tet.2018.06.064

    2018 doi

  39. [47]

    Fluorescence lifetime imaging microscopy: Fundamentals and advances in instrumentation, analysis, and applications

    Datta, R.; Heaster, T.M.; Sharick, J.T.; Gillette, A.A.; Skala, M.C. Fluorescence lifetime imaging microscopy: Fundamentals and advances in instrumentation, analysis, and applications. J. Biomed. Opt. 2020, 25, 071203. https://doi.org/10.1117/1.JBO.25.7.071203

    2020 doi

  40. [48]

    High-yield production of 2D crystals by wet- jet milling

    Del Rio Castillo, A.E.; Pellegrini, V.; Ansaldo, A.; Ricciardella, F.; Sun, H.; Marasco, L.; Buha, J.; Dang, Z.; Gagliani, L.; Lago, E.; et al. High-yield production of 2D crystals by wet- jet milling. Mater. Horizons 2018, 5, 890–904. https://doi.org/10.1039/c8mh00487k

    2018 doi

  41. [49]

    Raman Spectrum of Graphene and Graphene Layers

    Ferrari, A.C.; Meyer, J.C.; Scardaci, V.; Casiraghi, C.; Lazzeri, M.; Mauri, F.; Piscanec, S.; Jiang, D.; Novoselov, K.S.; Roth, S.; et al. Raman Spectrum of Graphene and Graphene Layers. Phys. Rev. Lett. 2006, 97, 187401. https://doi.org/10.1103/PhysRevLett.97.187401

    2006 doi

  42. [50]

    Quantifying Defects in Graphene via Raman 19 Spectroscopy at Different Excitation Energies

    Jorio, A.; Ferreira, E.H.M.; Stavale, F.; Achete, C.A.; Capaz, R.B.; Moutinho, M.V.O.; Lombardo, A.; Kulmala, T.S.; Ferrari, A.C. Quantifying Defects in Graphene via Raman 19 Spectroscopy at Different Excitation Energies. Nano Lett. 2011, 12, 3190–3196. https://doi.org/10.1021...

    2011 doi

  43. [51]

    Probing the nature of defects in graphene by Raman spectroscopy

    Eckmann, A.; Felten, A.; Mishchenko, A.; Britnell, L.; Krupke, R.; Novoselov, K.S.; Casiraghi, C. Probing the nature of defects in graphene by Raman spectroscopy. Nano Lett. 2012, 12, 3925–3930. https://doi.org/10.1021/nl300901a

    2012 doi

  44. [52]

    Raman study on defective graphene: Effect of the excitation energy , type , and amount of defects

    Eckmann, A.; Felten, A.; Verzhbitskiy, I.; Davey, R.; Casiraghi, C. Raman study on defective graphene: Effect of the excitation energy , type , and amount of defects. Phys. Rev. B 2013, 88, 035426. https://doi.org/10.1103/PhysRevB.88.035426

    2013 doi

  45. [53]

    Formation of arenicin-1 microdomains in bilayers and their specific lipid interaction revealed by Z-scan FCS

    MacHáň, R.; Hof, M.; Chernovets, T.; Zhmak, M.N.; Ovchinnikova, T.V.; Sýkora, J. Formation of arenicin-1 microdomains in bilayers and their specific lipid interaction revealed by Z-scan FCS. Anal. Bioanal. Chem. 2011, 399, 3547–3554. https://doi.org/10.1007/s00216- 011-4694-z

    2011 doi

  46. [54]

    Delamination and defects in graphene nanosheets exfoliated from 3D precursors

    Sethurajaperumal, A.; Ravichandran, V.; Merenkov, I.; Ostrikov (Ken), Varrla, E. Delamination and defects in graphene nanosheets exfoliated from 3D precursors. Carbon 2023, 213, 118306. https://doi.org/10.1016/j.carbon.2023.118306

    2023

  47. [55]

    Nature of graphene edges: A review

    Acik, M.; Chabal, Y.J. Nature of graphene edges: A review. Jpn. J. Appl. Phys. 2011, 50, 070101. https://doi.org/10.1143/JJAP.50.070101

    2011 doi

  48. [56]

    Characterization of new fluorescent labels for ultra-high resolution microscopy

    Chmyrov, A.; Arden-Jacob, J.; Zilles, A.; Drexhage, K.H.; Widengren, J. Characterization of new fluorescent labels for ultra-high resolution microscopy. Photochem. Photobiol. Sci. 2008, 7, 1378–1385. https://doi.org/10.1039/b810991p

    2008 doi

  49. [57]

    Ultrafast photoinduced dynamics of the 3,6-diaminoacridinium derivative ATTO 465 in solution

    Arden-Jacob, J.; Drexhage, K.H.; Druzhinin, S.I.; Ekimova, M.; Flender, O.; Lenzer, T.; Oum, K.; Scholz, M. Ultrafast photoinduced dynamics of the 3,6-diaminoacridinium derivative ATTO 465 in solution. Phys. Chem. Chem. Phys. 2013, 15 , 1844–1853. https://doi.org/10.1039/c2cp43493h

    2013 doi

  50. [58]

    Fluorescence-Lifetime-Sensitive Probes for Monitoring ATP Cleavage

    Hammler, D.; Marx, A.; Zumbusch, A. Fluorescence-Lifetime-Sensitive Probes for Monitoring ATP Cleavage. Chem. Eur. J . 2018, 24 , 15329–15335. https://doi.org/10.1002/chem.201803234

    2018 doi

  51. [59]

    Measuring sub-nanometer undulations at microsecond temporal resolution with metal- and graphene-induced energy transfer spectroscopy

    Chen, T.; Karedla, N.; Enderlein, J. Measuring sub-nanometer undulations at microsecond temporal resolution with metal- and graphene-induced energy transfer spectroscopy. Nat. Commun. 2024, 15, 1789. https://doi.org/10.1038/s41467-024-45822-x

    2024 doi

  52. [60]

    Xin, G.; Gong, S.; Kim, N.; Kim, J.; Hwang, W.; Nam, J.; Cho, Y.H.; Cho, S.M.; Chae, H.; Graphene oxide/N-methyl-2-pyrrolidone charge-transfer complexes for molecular detection. Sens. Actuators B Chem. 2013, 176, 81–85. https://doi.org/10.1016/j.snb.2012.09.003

    2013 doi

  53. [61]

    Fluorescence lifetime measurements and biological imaging

    Berezin, M.Y.; Achilefu, S. Fluorescence lifetime measurements and biological imaging. Chem. Rev. 2010, 110, 2641–2684. https://doi.org/10.1021/cr900343z. 20 Supporting Information for Surface grafting of graphene flakes with fluorescent dyes: a tailored functionalization appr...

    2010 doi

  54. [63]

    Analytical techniques and equipment 1.1 UHPLC-MS analysis of the linker molecule The linker molecule was analyzed and purified with an Ultra High Performance Liquid Chromatography (UHPLC) system (Shimadzu Nexera). The analyte was identified through a diode-array detector using...

    2015

  55. [1717]

    https://doi.org/10.3390/nano11071717

    doi

Pith tools

Reviewed August 15, 2026 · model on record in the stance chip above.