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Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Inorganic Chemistry".

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 21735

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Special Issue Editor

Dr. Raffaello Papadakis

E-Mail Website1 Website2
Guest Editor

TdB Labs, 75651 Uppsala, Sweden
Interests: organic synthesis; medium responsive compounds; graphene chemistry; solvatochromism; physical organic chemistry; solution chemistry; materials modifications and functionalization; polymer chemistry

Special Issue Information

Dear Colleagues,

In recent years, there has been a remarkable interest in graphene, predominantly because of its exceptional properties (both physical and chemical). A substantial part of current research on graphene deals with the development of novel methodologies, allowing the tailoring of its properties. These methodologies rely, in their vast majority, on covalent and noncovalent functionalizations which can provide access to novel materials with suitable properties for new technological applications. Specifically, functionalization of graphene with heterocyclic compounds attracts more and more attention. Multifunctional modifications of graphene via attachment of heterocycles or via heteroatom do** techniques can modulate its properties, and this can be vital for a number of applications, e.g., electronic, environmental, sensing applications, as well as catalysis. In line with the above trends, this Special Issue aims to cover new research and review this growing scientific field.

Dr. Raffaello Papadakis
Guest Editor

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Keywords

Graphene functionalizations
Heterocyclic chemistry
Covalent attachment of heterocycles
Noncovalent functionalization of graphene
Heteroatom-doped graphene
Catalysis
Tailoring the properties of graphene

Published Papers (7 papers)

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Research

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21 pages, 5715 KiB

Open AccessArticle

Graphene Nanoplatelets’ Effect on the Crystallization, Glass Transition, and Nanomechanical Behavior of Poly(ethylene 2,5-furandicarboxylate) Nanocomposites

by Dimitra Kourtidou, Maria-Eirini Grigora, Dimitrios Tzetzis, Dimitrios N. Bikiaris and Konstantinos Chrissafis

Molecules 2022, 27(19), 6653; https://doi.org/10.3390/molecules27196653 - 6 Oct 2022

Cited by 4 | Viewed by 1657

Abstract

Poly(ethylene 2,5-furandicarboxylate) (PEF) nanocomposites reinforced with various content of graphene nanoplatelets (GNPs) were synthesized in situ in this work. PEF is a widely known biobased polyester with promising physical properties and is considered as the sustainable counterpart of PET. Despite its exceptional gas barrier and mechanical properties, PEF presents with a low crystallization rate. In this context, a small number of GNPs were incorporated into the material to facilitate the nucleation and overall crystallization of the matrix. Kinetic analysis of both the cold and melt crystallization processes of the prepared materials was achieved by means of differential scanning calorimetry (DSC). The prepared materials’ isothermal crystallization from the glass and melt states was studied using the Avrami and Hoffman–Lauritzen theories. The Dobreva method was applied for the non-isothermal DSC measurements to calculate the nucleation efficiency of the GNPs on the PEF matrix. Furthermore, Vyazovkin’s isoconversional method was employed to estimate the effective activation energy values of the amorphous materials’ glass transition. Finally, the nanomechanical properties of the amorphous and semicrystalline PEF materials were evaluated via nanoindentation measurements. It is shown that the GNPs facilitate the crystallization process through heterogeneous nucleation and, at the same time, improve the nanomechanical behavior of PEF, with the semicrystalline samples presenting with the larger enhancements. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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19 pages, 4203 KiB

Open AccessArticle

Role of Functional Groups in the Monomer Molecule on the Radical Polymerization in the Presence of Graphene Oxide. Polymerization of Hydroxyethyl Acrylate under Isothermal and Non-Isothermal Conditions

by Ioannis S. Tsagkalias and Dimitrios S. Achilias

Molecules 2022, 27(2), 345; https://doi.org/10.3390/molecules27020345 - 6 Jan 2022

Cited by 5 | Viewed by 1748

Abstract

Functional groups in a monomer molecule usually play an important role during polymerization by enhancing or decreasing the reaction rate due to the possible formation of side bonds. The situation becomes more complicated when polymerization takes place in the presence of graphene oxide since it also includes functional groups in its surface. Aiming to explore the role of functional groups on polymerization rate, the in situ bulk radical polymerization of hydroxyethyl acrylate (HEA) in the presence or not of graphene oxide was investigated. Differential scanning calorimetry was used to continuously record the reaction rate under both isothermal and non-isothermal conditions. Simple kinetic models and isoconversional analysis were used to estimate the variation of the overall activation energy with the monomer conversion. It was found that during isothermal experiments, the formation of both inter- and intra-chain hydrogen bonds between the monomer and polymer molecules results in slower polymerization of neat HEA with higher overall activation energy compared to that estimated in the presence of GO. The presence of GO results in a dissociation of hydrogen bonds between monomer and polymer molecules and, thus, to higher reaction rates. Isoconversional methods employed during non-isothermal experiments revealed that the presence of GO results in higher overall activation energy due to the reaction of more functional groups on the surface of GO with the hydroxyl and carbonyl groups of the monomer and polymer molecules, together with the reaction of primary initiator radicals with the surface hydroxyl groups in GO. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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16 pages, 5141 KiB

Open AccessArticle

Polyethylene Glycol Functionalized Graphene Oxide Nanoparticles Loaded with Nigella sativa Extract: A Smart Antibacterial Therapeutic Drug Delivery System

by Mustafa A. Jihad, Farah T. M. Noori, Majid S. Jabir, Salim Albukhaty, Faizah A. AlMalki and Amal A. Alyamani

Molecules 2021, 26(11), 3067; https://doi.org/10.3390/molecules26113067 - 21 May 2021

Cited by 86 | Viewed by 4252

Abstract

Flaky graphene oxide (GO) nanoparticles (NPs) were synthesized using Hummer’s method and then capped with polyethylene glycol (PEG) by an esterification reaction, then loaded with Nigella sativa (N. sativa) seed extract. Aiming to investigate their potential use as a smart drug delivery system against Staphylococcus aureus and Escherichia coli, the spectral and structural characteristics of GO-PEG NPs were comprehensively analyzed by XRD, AFM, TEM, FTIR, and UV- Vis. XRD patterns revealed that GO-PEG had different crystalline structures and defects, as well as a higher interlayer spacing. AFM results showed GONPs with the main grain size of 24.41 nm, while GONPs–PEG revealed graphene oxide aggregation with the main grain size of 287.04 nm after loading N. sativa seed extract, which was verified by TEM examination. A strong OH bond appeared in FTIR spectra. Furthermore, UV- Vis absorbance peaks at (275, 284, 324, and 327) nm seemed to be correlated with GONPs, GO–PEG, N. sativa seed extract, and GO –PEG- N. sativa extract. The drug delivery system was observed to destroy the bacteria by permeating the bacterial nucleic acid and cytoplasmic membrane, resulting in the loss of cell wall integrity, nucleic acid damage, and increased cell-wall permeability. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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14 pages, 6235 KiB

Open AccessArticle

Exfoliation and Noncovalent Functionalization of Graphene Surface with Poly-N-Vinyl-2-Pyrrolidone by In Situ Polymerization

by Suguna Perumal, Raji Atchudan, Thomas Nesakumar Jebakumar Immanuel Edison, Jae-** Shim and Yong Rok Lee

Molecules 2021, 26(6), 1534; https://doi.org/10.3390/molecules26061534 - 11 Mar 2021

Cited by 13 | Viewed by 2504

Abstract

Heteroatom functionalization on a graphene surface can endow the physical and structural properties of graphene. Here, a one-step in situ polymerization method was used for the noncovalent functionalization of a graphene surface with poly-N-vinyl-2-pyrrolidone (PNVP) and the exfoliation of graphite into graphene sheets. The obtained graphene/poly-N-vinyl pyrrolidone (GPNVP) composite was thoroughly characterized. The surface morphology of GPNVP was observed using field emission scanning electron microscopy and high-resolution transmission electron microscopy. Raman spectroscopy and X-ray diffraction studies were carried out to check for the exfoliation of graphite into graphene sheets. Thermogravimetric analysis was performed to calculate the amount of PNVP on the graphene surface in the GPNVP composite. The successful formation of the GPNVP composite and functionalization of the graphene surface was confirmed by various studies. The cyclic voltammetry measurement at different scan rates (5–500 mV/s) and electrochemical impedance spectroscopy study of the GPNVP composite were performed in the typical three-electrode system. The GPNVP composite has excellent rate capability with the capacitive property. This study demonstrates the one-pot preparation of exfoliation and functionalization of a graphene surface with the heterocyclic polymer PNVP; the resulting GPNVP composite will be an ideal candidate for various electrochemical applications. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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Review

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21 pages, 4519 KiB

Open AccessReview

Graphene-Oxide-Based Fluoro- and Chromo-Genic Materials and Their Applications

by **aoxiao Zheng, Rongli Zhai, Zihao Zhang, Baoqing Zhang, Jiangwei Liu, Aamir Razaq, Muhammad Ashfaq Ahmad, Rizwan Raza, Muhammad Saleem, Syed Rizwan, Syed Hassan Mujtaba Jafri, Hu Li and Raffaello Papadakis

Molecules 2022, 27(6), 2018; https://doi.org/10.3390/molecules27062018 - 21 Mar 2022

Cited by 5 | Viewed by 3346

Abstract

Composite materials and their applications constitute a hot field of research nowadays due to the fact that they comprise a combination of the unique properties of each component of which they consist. Very often, they exhibit better performance and properties compared to their combined building blocks. Graphene oxide (GO), as the most widely used derivative of graphene, has attracted widespread attention because of its excellent properties. Abundant oxygen-containing functional groups on GO can provide various reactive sites for chemical modification or functionalization of GO, which in turn can be used to develop novel GO-based composites. This review outlines the most recent advances in the field of novel dyes and pigments encompassing GO as a key ingredient or as an important cofactor. The interactions of graphene with other materials/compounds are highlighted. The special structure and unique properties of GO have a great effect on the performance of fabricated hybrid dyes and pigments by enhancing the color performance of dyes, the anticorrosion properties of pigments, the viscosity and rheology of inks, etc., which further expands the applications of dyes and pigments in dyeing, optical elements, solar-thermal energy storage, sensing, coatings, and microelectronics devices. Finally, challenges in the current development as well as the future prospects of GO-based dyes and pigments are also discussed. This review provides a reference for the further exploration of novel dyes and pigments. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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19 pages, 6022 KiB

Open AccessReview

Graphene Oxide-Based Stimuli-Responsive Platforms for Biomedical Applications

by Tejal V. Patil, Dinesh K. Patel, Sayan Deb Dutta, Keya Ganguly and Ki-Taek Lim

Molecules 2021, 26(9), 2797; https://doi.org/10.3390/molecules26092797 - 10 May 2021

Cited by 35 | Viewed by 4279

Abstract

Graphene is a two-dimensional sp² hybridized carbon material that has attracted tremendous attention for its stimuli-responsive applications, owing to its high surface area and excellent electrical, optical, thermal, and mechanical properties. The physicochemical properties of graphene can be tuned by surface functionalization. The biomedical field pays special attention to stimuli-responsive materials due to their responsive abilities under different conditions. Stimuli-responsive materials exhibit great potential in changing their behavior upon exposure to external or internal factors, such as pH, light, electric field, magnetic field, and temperature. Graphene-based materials, particularly graphene oxide (GO), have been widely used in stimuli-responsive applications due to their superior biocompatibility compared to other forms of graphene. GO has been commonly utilized in tissue engineering, bioimaging, biosensing, cancer therapy, and drug delivery. GO-based stimuli-responsive platforms for wound healing applications have not yet been fully explored. This review describes the effects of different stimuli-responsive factors, such as pH, light, temperature, and magnetic and electric fields on GO-based materials and their applications. The wound healing applications of GO-based materials is extensively discussed with cancer therapy and drug delivery. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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16 pages, 528 KiB

Open AccessReview

Green Bioanalytical Applications of Graphene Oxide for the Extraction of Small Organic Molecules

by Natalia Manousi, Orfeas-Evangelos Plastiras, Eleni A. Deliyanni and George A. Zachariadis

Molecules 2021, 26(9), 2790; https://doi.org/10.3390/molecules26092790 - 9 May 2021

Cited by 6 | Viewed by 2791

Abstract

Bioanalysis is the scientific field of the quantitative determination of xenobiotics (e.g., drugs and their metabolites) and biotics (e.g., macromolecules) in biological matrices. The most common samples in bioanalysis include blood (i.e., serum, plasma and whole blood) and urine. However, the analysis of alternative biosamples, such as hair and nails are gaining more and more attention. The main limitations for the determination of small organic compounds in biological samples is their low concentration in these matrices, in combination with the sample complexity. Therefore, a sample preparation/analyte preconcentration step is typically required. Currently, the development of novel microextraction and miniaturized extraction techniques, as well as novel adsorbents for the analysis of biosamples, in compliance with the requirements of Green Analytical Chemistry, is in the forefront of research in analytical chemistry. Graphene oxide (GO) is undoubtedly a powerful adsorbent for sample preparation that has been successfully coupled with a plethora of green extraction techniques. GO is composed of carbon atoms in a sp² single-atom layer of a hybrid connection, and it exhibits high surface area, as well as good mechanical and thermal stability. In this review, we aim to discuss the applications of GO and functionalized GO derivatives in microextraction and miniaturized extraction techniques for the determination of small organic molecules in biological samples. Full article

(This article belongs to the Special Issue Graphene Oxide and Heterocycle-Involving Graphene Analogues: Syntheses, Functionalizations, Interactions and Catalysis)

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