Edge‐Functionalized Nanographenes

Sekiya, Ryo; Haino, Takeharu

doi:10.1002/chem.202003370

Cited by 22 publications

(22 citation statements)

References 106 publications

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“…The bottom-up method produces NGs from small organic molecules and can be subdivided into two categories. [34][35] One approach is to utilize carbon-carbon bond formations by organic reactions, allowing the realization of structurally well-defined carbon frameworks, and the other is to produce NGs by carbonization of small molecules under harsh reaction conditions such as hydrothermal reactions. Although the former protocols require multi-step synthesis, the structurally well-defined carbon frameworks secure the repro- ducibility of their properties.…”

Section: Production Of Nanographenesmentioning

confidence: 99%

“…These methods have been reviewed in various papers [12–15,18] and we briefly introduce these methods. The bottom‐up method produces NGs from small organic molecules and can be subdivided into two categories [34–35] . One approach is to utilize carbon‐carbon bond formations by organic reactions, allowing the realization of structurally well‐defined carbon frameworks, and the other is to produce NGs by carbonization of small molecules under harsh reaction conditions such as hydrothermal reactions.…”

Section: Functionalization Of Nanographenesmentioning

confidence: 99%

“…The first step was to install organic substituents at the edge of NGs in a polar solvent to improve their affinity for less polar organic solvents [35] . We installed p ‐propargyloxybenzyl amine ( U1 ) into the edge [33] .…”

Section: Functionalization Of Nanographenesmentioning

confidence: 99%

“…The first step was to install organic substituents at the edge of NGs in a polar solvent to improve their affinity for less polar organic solvents. [35] We installed p-propargyloxybenzyl amine (U1) into the edge. [33] The triple bond enables us to conduct a Cu(I)-catalyzed Huisgen cycloaddition reaction (click reaction).…”

Section: Nanographenes In Organic Solventsmentioning

confidence: 99%

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Nanographene – A Scaffold of Two‐Dimensional Materials

Sekiya

Haino

2021

The Chemical Record

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Substances can be divided into 0D to 3D species based on the number of repeating units (atom, ion, and molecule) and their arrangements in space (point, linear, layer, and solid). Discrete substances belong to 0D species, polymers are examples of 1D species, and molecular crystals are 3D species. Most of the substances belong to one of these species. On the other hand, those categorized into 2D species wherein the repeating units organize a layer are less explored. 2D species have a surface and edges. The incorporation of these structural features into a molecular design can realize multifunctionalized systems that are difficult to achieve by conventional organic synthesis. The development of 2D species is, therefore, the frontier of organic, inorganic, and polymer chemistry. Nanographenes (NGs) are suitable scaffolds for realizing 2D species due to several factors, such as chemical stability and oxygen-containing functional groups on the surface and on the edge, allowing postsynthetic modifications. Our group has utilized NGs with tens of nanometers in diameters for developing 2D species. Carboxy groups on the edge enable us to install various substituents into NGs, offering NG-based functional materials. These studies demonstrate that the integration of NGs with organic chemistry can widen the scope of their applications other than optical materials that are a main application of NGs. We introduce our recent studies on the development of NG-based functional materials realized by postsynthetic modifications. We hope that this account will contribute to the development of the chemistry of 2D species.

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Section: Production Of Nanographenesmentioning

confidence: 99%

Section: Functionalization Of Nanographenesmentioning

confidence: 99%

Section: Functionalization Of Nanographenesmentioning

confidence: 99%

Section: Nanographenes In Organic Solventsmentioning

confidence: 99%

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Nanographene – A Scaffold of Two‐Dimensional Materials

Sekiya

Haino

2021

The Chemical Record

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“…This process can be even more improved by using surfactants [ 6 ]. Starting from pristine raw graphene, different derivatives have been synthetized, among which the most versatile are graphene oxide (GO), reduced graphene oxide (rGO), nanographenes (NGs), and graphene nanoribbons [ 7 ]. GO results from the chemical exfoliation and oxidation of layered crystalline graphite, while rGO is derived from the removal of oxygen groups from GO by reducing chemical agents, such as hydrazine, ascorbic acid, and many others, or through thermal or UV treatment of GO [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Graphene-Oxide-Enriched Biomaterials: A Focus on Osteo and Chondroinductive Properties and Immunomodulation

et al. 2022

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Due to its exceptional physical properties, such as high electronic conductivity, good thermal stability, excellent mechanical strength, and chemical versatility, graphene has sparked a lot of interest in the scientific community for various applications. It has therefore been employed as an antibacterial agent, in photothermal therapy (PTT) and biosensors, in gene delivery systems, and in tissue engineering for regenerative purposes. Since it was first discovered in 1947, different graphene derivatives have been synthetized from pristine graphene. The most adaptable derivate is graphene oxide (GO). Owing to different functional groups, the amphiphilic structure of GO can interact with cells and exogenous or endogenous growth/differentiation factors, allowing cell adhesion, growth, and differentiation. When GO is used as a coating for scaffolds and nanomaterials, it has been found to enhance bone, chondrogenic, cardiac, neuronal, and skin regeneration. This review focuses on the applications of graphene-based materials, in particular GO, as a coating for scaffolds in bone and chondrogenic tissue engineering and summarizes the most recent findings. Moreover, novel developments on the immunomodulatory properties of GO are reported.

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Curved Nanographenes: Multiple Emission, Thermally Activated Delayed Fluorescence, and Non‐Radiative Decay

et al. 2023

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The intriguing and rich photophysical properties of three curved nanographenes (CNG 6, 7, and 8) are investigated by time‐resolved and temperature‐dependent photoluminescence (PL) spectroscopy. CNG 7 and 8 exhibit dual fluorescence, as well as dual phosphorescence at low temperature in the main PL bands. In addition, hot bands are detected in fluorescence as well as phosphorescence, and, in the narrow temperature range of 100–140 K, thermally activated delayed fluorescence (TADF) with lifetimes on the millisecond time‐scale is observed. These findings are rationalized by quantum‐chemical simulations, which predict a single minimum of the S1 potential of CNG 6, but two S1 minima for CNG 7 and CNG 8, with considerable geometric reorganization between them, in agreement with the experimental findings. Additionally, a higher‐lying S2 minimum close to S1 is optimized for the three CNG, from where emission is also possible due to thermal activation and, hence, non‐Kasha behavior. The presence of higher‐lying dark triplet states close to the S1 minima provides mechanistic evidence for the TADF phenomena observed. Non‐radiative decay of the T1 state appears to be thermally activated with activation energies of roughly 100 meV and leads to disappearance of phosphorescence and TADF at T > 140 K.

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Edge‐Functionalized Nanographenes

Abstract: Selected by the EditorialO ffice for our Showcaseo fo utstanding Reviewtype articles (www.chemeurj.org/showcase).

Cited by 22 publications

References 106 publications

Nanographene – A Scaffold of Two‐Dimensional Materials

Nanographene – A Scaffold of Two‐Dimensional Materials

Graphene-Oxide-Enriched Biomaterials: A Focus on Osteo and Chondroinductive Properties and Immunomodulation

Curved Nanographenes: Multiple Emission, Thermally Activated Delayed Fluorescence, and Non‐Radiative Decay

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