A C₆₀-aryne building block: synthesis of a hybrid all-carbon nanostructure

Abstract

The synthesis of a [60]fullerene-benzyne building block and its further chemical cycloaddition reaction with graphene has resulted in a new all-carbon hybrid material which has been characterized by TGA, FTIR and Raman spectroscopies, XPS as well as AFM and TEM. Based on computational studies, the formation of both [2+2] and [4+2] cycloadducts on the graphene surface is feasible.

Exploring Tetrathiafulvalene–Carbon Nanodot Conjugates in Charge Transfer Reactions

“…[36] Thesame components were used to fit the C1score-level region in pCNDs (Supporting Information, Figure S8). The presence of the characteristic p-p*shake up of carbon atoms in graphene-like structures [37] is in agreement with the TGA and Raman analyses and prompts to some graphitic character of the CND materials.T EM and AFM further supports the notion of p-p*s hake up bands,s ince the presence of small aggregates together with individual pCNDs are observed (Supporting Information, Figures S2 and S3). Thef it of the N1sl ine of pCND-exTTF shows four different chemical components centered at 398.5 (pyridinic N), 399.3 (amine), 400.0 (pyrrolic N), and 401.0 eV (graphitic N).…”

Hybrids of Fullerenes and 2D Nanomaterials

“…[18] C 60 reacted with 2,5-bis(trimethylsilyl)-1,4-phenylene bis(triflate) via a [2 + 2] cycloaddition yielding a C 60 -aryne precursor (Figure 16A), which reacted further with pristine graphene. [18] C 60 reacted with 2,5-bis(trimethylsilyl)-1,4-phenylene bis(triflate) via a [2 + 2] cycloaddition yielding a C 60 -aryne precursor (Figure 16A), which reacted further with pristine graphene.…”

“…[18] C 60 reacted with 2,5-bis(trimethylsilyl)-1,4-phenylene bis(triflate) via a [2 + 2] cycloaddition yielding a C 60 -aryne precursor (Figure 16A), which reacted further with pristine graphene. [18] In addition to above-mentioned binary fullerene-graphene hybrids, the inclusion of another functional material to form ternary hybrids with fullerene and graphene as building blocks has also been reported. According to theoretical calculations, the hybrid was proposed to be a [4 + 2] cycloadduct, which was the more stable configuration to be formed ( Figure 16B), while the formation of [2 + 2] cycloadducts also seemed possible because of the small difference in energy.…”

“…[35] They first prepared a selfassembled monolayer of (3-aminopropyl)triethoxysilane (APTES) covalently anchored onto the silicon wafer via SiOSi covalent bonding, followed by covalently attaching GO onto the APTES-self-assembled monolayer (SAM) surface through chemical reactions between epoxy-carboxyl and amine groups. [18] Copyright 2016, the Royal Society of Chemistry. The successful grafting of C 60 chemically to the amine-functional GO by nucleophilic addition reactions was verified by FTIR, X-ray powder diffraction (XRD), TGA, Raman spectroscopy and XPS.…”

Modulation of the exfoliated graphene work function through cycloaddition of nitrile imines

“…22 Although numerous cycloaddition reactions have been explored experimentally with fullerenes 23 or carbon nanotubes, 24 and despite the fact that the covalent functionalization of graphene is a growing field of research, only the 1,3-dipolar cycloaddition of azomethine ylides 14,15 has been applied to the functionalization of graphene. [25][26][27][28] The band gap and the work function (WF) of a material provide information about the electronic states on the surface of the solid and most organic electronic devices require the use of semiconducting materials in which the work function should be adjustable, thus allowing efficient charge transport. In this sense, the possibility of adjusting the work function through chemical functionalization makes graphene a very promising material in the semiconductor field.…”