Electrochromism of Nanographenes in the Near‐Infrared Region

Matsumoto, Ikuya; Sekiya, Ryo; Fukui, Hiroki; Sun, Ren‐De; Haino, Takeharu

doi:10.1002/anie.202200291

Cited by 16 publications

(14 citation statements)

References 41 publications

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“…The utilization of the electronic interactions between NG and an installed organic substituent can be effective in regulating the absorption of light. [39] The installation of triphenylamines into the edge realized NG-based electrochromic materials displaying the electrochromic function from the visible to NIR region.…”

Section: Purification and Characterizationmentioning

confidence: 99%

“…[25] Edge Functionalization Organic substituents can influence the physical properties of NGs. Reported examples indicate that the solubility, [36] photoemission properties, [31] and electronic properties [39] of NGs can be manipulated by the installed organic substituents.…”

Section: Purification and Characterizationmentioning

confidence: 99%

“…The photoluminescence wavelength in water experienced a redshift with the order of ethylene‐1,2‐diamine (486 nm) and o ‐phenylenediamine (502 nm) compared to unfunctionalized NGs (455 nm), likely due to the extension of the π system that narrows the bandgap. The utilization of the electronic interactions between NG and an installed organic substituent can be effective in regulating the absorption of light [39] . The installation of triphenylamines into the edge realized NG‐based electrochromic materials displaying the electrochromic function from the visible to NIR region.…”

Section: Introductionmentioning

confidence: 99%

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Integration of Nanographenes and Organic Chemistry – Toward Nanographene‐based Two‐Dimensional Materials

Sekiya

Haino

2022

ChemPhysChem

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Graphene and its relatives have received considerable attention from the fields of physics and chemistry since the isolation of pristine graphene sheets. Nanographenes (NGs) are graphene fragments that are a few to tens of nanometers in diameter. Compared to graphene and its relatives, such as graphene oxides, NGs can be handled more easily, and their large π surface and oxygen functional groups on the edge allow postsynthetic modifications. The study of NGs is gradually shifting from the development of synthetic procedures to postsynthetic modification. From the structural point of view, NGs can be regarded as two-dimensional carbon polymers. Their unique structures and affinity for organic molecules make NGs excellent scaffolds for two-dimensional materials, which are now an important topic in organic and polymer chemistry. In this conceptual article, we introduce the position of NGs from the perspective of two-dimensional substances and briefly review both the structural features of NGs and the effects of functionalization on their physical properties. These are valuable when producing reasonable strategies for their postsynthetic modifications.

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Section: Purification and Characterizationmentioning

confidence: 99%

Section: Purification and Characterizationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Integration of Nanographenes and Organic Chemistry – Toward Nanographene‐based Two‐Dimensional Materials

Sekiya

Haino

2022

ChemPhysChem

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“…[3][4][5][6][7][8][9] Our group has developed NG-based hybrid systems via edge functionalization of NGs produced by a top-down method. [10] These NGs displayed unique functionalities, such as photoemission, [11][12][13][14] self-organization, [15] electrochromism, [16] and catalytic activity. [17] Their large hexagonally arranged sp 2 carbon frameworks allowed the NGs to be used as scaffolds for two-dimensional materials.…”

Section: Introductionmentioning

confidence: 99%

Induction of Chirality on Nanographenes

Arimura

Matsumoto

Nishitani

et al. 2023

Chemistry An Asian Journal

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Chirality induction is an important topic in studies of nanographenes (NGs). We report chirality enhancements of NGs through postsynthetic chemical modifications of NGs with pyrene and m-terphenyl groups. These substituents were installed into N-(p-bromophenylethyl)imides on the edges of the NGs with Pd-catalyzed cross-coupling reactions. Circular dichroism (CD) spectra demonstrated that these bulky substituents improved the induced CD signal of the NGs compared to those previously reported and suggested that they induced the opposite chirality. Density functional theory calculations indicated possible edge structures for the NGs and indicated that π/π and CH/π interactions among the neighboring substituents influenced the orientations of the imides. These imides distorted the edges, and the distorted edges eventually generated the chiral environments of the NGs. The interactions among the substituents are, therefore, likely to allow detection of the CD signals in the visible region and induction of the opposite chirality.

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“…Top-down methods produce NGs from various carbon sources and have been employed for the fabrication of carbon-based functional materials. [5][6] Chemical functionalization makes them lipophilic and can regulate their physical properties and/or add new functions to them, [5][6][7][8][9][10][11][12][13][14][15][16][17] demonstrating that NGs are excellent scaffolds of functional materials. [18] Understanding the effects of installed substituents on the physical properties of NGs is, therefore, crucial for advancing this field, and computational studies are suitable for that.…”

Section: Introductionmentioning

confidence: 99%

Computational Studies on the Structures of Nanographenes with Various Edge Functionalities

2022

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Computational studies have often been carried out on hydrogen-terminated nanographenes (NGs). These structures are, however, far from those deduced from experimental observations, which have suggested armchair edges with two carboxy groups on the edges as dominant. We conducted computational studies on NGs consisting of C 42 , C 60 , C 78 , C 96 , C 142 , and C 174 carbon atoms with hydrogen, carboxy, and N-methyl imideterminated armchair edges. DFT calculations inform distorted basal planes and similar HOMO-LUMO gaps, indicating that the edge oxidation and functionalization do not very influence the electronic structure. Comparison of observed UV-vis spectra of carboxy-and N-octadecyl chain terminated NGs with calculated spectra of model NGs informs the contribution of π-π* transitions on the basal plane to the absorptions in the visible region. A dimeric structure of NG and octadecyl-installed NG demonstrate that both the distorted basal planes and the steric contacts among the functional groups widen the surface-tosurface distance thereby allowing the invasion of solvent molecules between the surfaces. This picture is consistent with the improved solubility of edge-modified NGs.

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Electrochromism of Nanographenes in the Near‐Infrared Region

Cited by 16 publications

References 41 publications

Integration of Nanographenes and Organic Chemistry – Toward Nanographene‐based Two‐Dimensional Materials

Integration of Nanographenes and Organic Chemistry – Toward Nanographene‐based Two‐Dimensional Materials

Induction of Chirality on Nanographenes

Computational Studies on the Structures of Nanographenes with Various Edge Functionalities

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