2002
DOI: 10.1002/1521-3765(20020315)8:6<1424::aid-chem1424>3.0.co;2-z
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Synthesis of a Giant 222 Carbon Graphite Sheet

Abstract: In this paper we present the synthesis and characterization of the so far largest polycyclic aromatic hydrocarbon (PAH), containing 222 carbon atoms or 37 separate benzene units. First a suitable three‐dimensional oligophenylene precursor molecule is built up by a sequence of Diels–Alder and cyclotrimerization reactions and then planarized in the final step by oxidative cyclodehydrogenation to the corresponding hexagonal PAH. Structural proof is based on isotopically resolved MALDI‐TOF mass spectra and electro… Show more

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Cited by 364 publications
(235 citation statements)
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“…Elemental analysis of 2 could not be obtained, due to incomplete combustion, an artifact of the extremely high thermal stability of the aromatic core of 1. 14 Confirmation of the bidentate nature of the coordination was obtained by comparing the 1 H NMR spectrum of 2 in CDCl 3 with that of the free ligand. The atom-labeling scheme is shown in Scheme 1.…”
Section: Resultsmentioning
confidence: 97%
“…Elemental analysis of 2 could not be obtained, due to incomplete combustion, an artifact of the extremely high thermal stability of the aromatic core of 1. 14 Confirmation of the bidentate nature of the coordination was obtained by comparing the 1 H NMR spectrum of 2 in CDCl 3 with that of the free ligand. The atom-labeling scheme is shown in Scheme 1.…”
Section: Resultsmentioning
confidence: 97%
“…Bottom-up, solution-based synthetic routes for graphene quantum dots (GQDs) are based on Diels-Alder, cyclotrimerization and/or cyclodehydrogenation reactions 12 to control the GN size 13,14 . However, these chemistries fail for more than 100 ringed GQDs [13][14][15][16][17] . This is attributed to the challenge in the synthesis/stabilization of precursors, and to the decrease in solubility of the poly-aromatics in the synthesis solvents 12,18 .…”
mentioning
confidence: 99%
“…68 Nanographene composed of 222 carbon atoms (37 fused benzene rings, Figure 6a), without solubilizing substituents was prepared by oxidation of the precursor polyphenylene using Cu(OTf) 2 and AlCl 3 at 30 1C for 1 day. 69 The product was insoluble due to the lack of side chains, but its structure was confirmed by solid state 13 C NMR and MALDI-TOF.…”
Section: Nanoscale Assembly T Emrick and E Pentzermentioning
confidence: 99%