Functionalized carbon nanomaterials
The era of carbon nanomaterials has started with the first reports on fullerenes and related compounds in the mid-eighties, and a tremendous increase of the research activity in the field has been observed ever since. New classes of carbon materials have entered the scene such as carbon nanotubes, carbon onions, nanoscale diamond and diamondoids. A major turning point was the appearance of graphene as a material available for in-depth investigations – spurred by the development of reliable production methods. The progress in terms of understanding the properties and chemistry of carbon nanomaterials has opened a whole new world of applications for nanomaterials in general. The present Thematic Series attempts to showcase the diversity in the field of carbon nanomaterials and carbon-rich compounds and to emphasize the links between the different classes of materials. Contributions from synthetic organic chemistry dealing with the formation and functionalization of carbon-rich molecules and from the area of functional nanomaterials illustrate the plethora of research activities.
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- Published 05 Feb 2014
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Figure 1: Structures of triads 1–6 and precursor molecules 7–8 used for the synthesis of the asymmetric syste...
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Scheme 1: The one-step synthetic procedure towards the oxalate-bridged fullerene triads 4 and 6.
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Scheme 2: Attempted synthetic pathway towards the formation of the C60–C70 oxalate bridged fullerene triad al...
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Scheme 3: Synthetic pathway to the asymmetric fullerene triad 5 allowing introduction of the fullerene cages ...
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Figure 2: Cyclic voltammograms of the terephthalate bridged triads 1–3 (left) and oxalate bridged triads 4–6 ...
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Figure 3: Fluid solution EPR spectra recorded at 297 K for the two electron reduced species of compounds 1 an...
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Figure 4: Frozen solution EPR spectra of triads 42− (a) and 12− (c), prepared by two electron reduction of 4 ...
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- Published 24 Mar 2014
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Figure 1: FTIR spectra of a) ND50-PG, b) ND-PG-OTs, c) ND-PG-N3, d) ND-PG-Arg8, e) ND-PG-Lys8, and f) ND-PG-H...
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Figure 2: 1H NMR spectra of a) ND50-PG, b) ND-PG-OTs and c) ND-PG-N3 in D2O.
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Figure 3: TGA profiles of ND50-PG under nitrogen and air.
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Figure 4: STEM images of a) pristine ND50 and b) ND50-PG.
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Scheme 1: Synthetic route from ND50 to ND-PG-BPP; i) glycidol, 140 °C, 20 h; ii) p-TsCl, pyridine, 0 °C to rt...
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Figure 5: Picture of the dispersions of a) ND50-PG (20 mg/mL), b) ND-PG-Arg8, c) ND-PG-Lys8 and d) ND-PG-His8...
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Figure 6: Electrophoretic migration of pDNA, NP (ND50-PG or ND-PG-BPP), and NP/pDNA mixtures at various weigh...
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Thermodynamically stable [4 + 2] cycloadducts of lanthanum-encapsulated endohedral metallofullerenes
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- Published 25 Mar 2014
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Scheme 1: Synthesis of [4 + 2] adducts of La2@C80.
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Figure 1: HPLC profiles of the reaction solutions (black) before and (red) after the reaction of La2@C80 and ...
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Figure 2: MALDI–TOF mass (negative mode) spectra of (a) 3b and (b) 4b, using 1,1,4,4-tetraphenyl-1,3-butadien...
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Figure 3: UV–vis/near-IR absorption spectra of 3b and 4b recorded by the diode array detector of the HPLC app...
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Figure 4: MALDI–TOF mass spectrum (negative mode) of the reaction mixture from La2@C80 and 1a, using 1,1,4,4-...
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Figure 5: 1H NMR spectra of (a) the mixture of 3a and 4a in C2D2Cl4 at 248 K, and (b) isolated 4a at 230 K, r...
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Figure 6: HPLC profiles of the mixture of 3a and 4a, (a) after heating in refluxing 1,2-dichlorobenzene and (...
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Figure 7: HPLC profiles of the reaction mixture of 3b and 4b, (black) before and (red) after heating in reflu...
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Figure 8: UV–vis/near-IR absorption spectra of 3b and 4a in toluene.
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Figure 9: Temperature-dependent 1H NMR spectra of 4a in C2D2Cl4 (left) at 300 MHz, and (right) at 500 MHz for...
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Scheme 2: Synthesis of [4 + 2] adducts of La@C82.
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Figure 10: HPLC profiles of the reaction mixture for 5b. Conditions: column, Buckyprep (Ø 4.6 mm × 250 mm); el...
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Figure 11: MALDI–TOF mass spectra (negative mode) of 5b, using 1,1,4,4-tetraphenyl-1,3-butadiene as matrix.
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Figure 12: Vis–near-IR spectra of 5b, 6 and La@C82 in CS2.
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Figure 13: 1H NMR spectrum of [5b]− in acetone-d6/CS2 (3/1 = v/v) at 223 K.
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Figure 14: 13C NMR spectrum of [5b]− in acetone-d6/CS2 (3/1 = v/v).
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Figure 15: HPLC profiles for comparison of the thermal stabilities of (a) 5b and (b) 6 at 30 °C. Conditions: c...
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- Published 11 Apr 2014
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Figure 1: Columnar packing structures of buckybowls showing (a) unidirectional and (b) opposite structures, i...
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Scheme 1: Synthesis of pyrenylsumanene (1): (a) Sc(OTf)3 (5 mol %), DIH (100 mol %), CH2Cl2, rt, 2.5 h, yield...
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Figure 2: The X-ray crystal structure of 1, showing: (a) top view of the ORTEP drawing with 50% probability, ...
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Figure 3: (a) Absorption spectra of 1, 3 and pyrene in CH2Cl2 solution (1.0 × 10−5 M); (b) emission spectra o...
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Figure 4: Calculated HOMO and LUMO orbitals and HOMO–LUMO gaps (ΔE) for 1, 3 and pyrene (ωB97XD/6-31G(d)).
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- Published 28 Apr 2014
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Figure 1: Prototypical open and closed geodesic polyarenes.
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Figure 2: Planar vs pyramidalized π-system.
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Figure 3: Selected examples of geodesic polyarenes synthesized by FVP.
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Scheme 1: Covalent functionalization of fullerene C60 by the Bingel–Hirsch reaction and the Prato reaction.
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Scheme 2: Fullerene-type chemistry at interior carbon atoms of corannulene (1) and diindenochrysene (10).
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Figure 4: POAV angles of fullerene C60 (2), corannulene (1), and diindenochrysene (10).
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Scheme 3: Synthesis of circumtrindene (6) by FVP.
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Scheme 4: Synthetic route to 3,9,15-trichlorodecacyclene (12).
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Figure 5: POAV angle and bond lengths of circumtrindene.
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Scheme 5: Bingel–Hirsch reaction of circumtrindene (6).
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Scheme 6: Proposed mechanism for the Bingel–Hirsch reaction of circumtrindene (6).
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Scheme 7: Prato reaction of circumtrindene (6).
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Figure 6: LUMO orbital map of circumtrindene (B3LYP/6-31G*). The darkest blue areas correspond to the regions...
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Figure 7: Electrostatic potentials on the surfaces of circumtrindene (B3LPY/6-31G*).
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Figure 8: Monoindeno- (25), diindeno- (26), and triindenocircumtrindene (27).
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Figure 9: Two different types of rim carbon atoms on circumtrindene.
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Scheme 8: Site-selective peripheral monobromination of circumtrindene.
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Scheme 9: Suzuki coupling and ring-closing reactions toward indenocircumtrindene (25).
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Scheme 10: Suzuki coupling to prepare compound 30.
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Figure 10: Chemical shifts of ortho-methyl groups in 30 and 31.
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- Published 06 Jun 2014
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Scheme 1: Synthesis of macrocycles 3 and 4.
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Figure 1: 1H NMR spectra of macrocycles 3a–d, with key proton resonances for the spacing units and key benzyl...
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Figure 2: 1H NMR spectroscopy of macrocycles 4a–d, with proton resonances for the spacing units and key benzy...
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Figure 3: CD spectra of macrocycles 3b, 3d, 4b, 4d in EtOH (0.5–12 × 10−6 M).
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Figure 4: UV–vis titration of C60 (1.8 × 10−4 M) in toluene with increasing amounts of macrocycle 4b (top) an...
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- Published 15 Jul 2014
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Figure 1: Structures of PAM1 to PAM3.
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Scheme 1: Synthetic pathway to PAM2 and PAM3.
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Figure 2: Scanning electron microscopy (SEM) images of PAM2 xerogel in cyclohexane (10 mg/mL). Scales are a) ...
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Figure 3: UV–vis spectrum of PAM2 before (black) and after (red) polymerization (PDA).
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Figure 4: Background-corrected Raman spectra of PAM2 (red) and the blue material obtained after UV irradiatio...
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- Published 28 Jul 2014
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Figure 1: a) Examples of common pentacene functionalization patterns and b) unsymmetrically aryl-substituted ...
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Scheme 1: Synthesis of unsymmetrically substituted pentacenes by nucleophilic addition (yields given are for ...
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Scheme 2: Functionalization of iodoaryl pentacene 3g using the Suzuki–Miyaura cross-coupling reaction.
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Figure 2: UV–vis spectra of pentacenes a) 3a–c and b) 3i–k (measured in CH2Cl2).
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Figure 3: UV–vis spectra of thin films (drop cast on quartz from a CH2Cl2 solution) for pentacenes a) 3a–c an...
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Figure 4: Schematic classification of three common solid-state arrangements of pentacene derivatives a) herri...
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Figure 5: X-ray crystallographic analysis of 3a showing a) molecular structure and b) packing motif (triisopr...
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Figure 6: X-ray crystallographic analysis of 3b showing a) molecular structure and b) packing motif (triisopr...
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Figure 7: X-ray crystallographic analysis of 3c showing a) molecular structure and b) packing motif (triisopr...
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Figure 8: X-ray crystallographic analysis of 3d showing a) molecular structure, and b) packing motif (triisop...
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Figure 9: X-ray crystallographic analysis of 3g showing a) molecular structure and b) packing motif; ORTEP dr...
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Figure 10: X-ray crystallographic analysis of 3h showing a) molecular structure and b) packing motif (triethyl...
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Figure 11: X-ray crystallographic analysis of 3i showing a) molecular structure and b) packing motif (triisopr...
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Figure 12: X-ray crystallographic analysis of 3j showing a) molecular structure and b) packing motif (triisopr...
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- Published 20 Nov 2014
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Scheme 1: Synthesis of nanodiamond derivatives carrying primary amino groups. a) Δ, b) 18-crown-6, KI, c) BH3...
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Figure 1: FTIR-spectra of annealed nanodiamond 2 (a), nitrile 4 (b) and amine 5 (c). As can be seen from the ...
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Figure 2: FTIR spectra (left) of compounds 2 (a), 9 (b), 10 (c) and 11 (d). The formation of the sulfone grou...
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Figure 3: Modified Kaiser test. a) Left: control, right: positive result; b) left: control, control with prem...
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- Published 26 Nov 2014
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Figure 1: Proposed functional groups on purified DND surface.
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Scheme 1: Overview on applied modification techniques to obtain DND with phosphate groups; conditions and rea...
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Figure 2: ATR-FTIR spectra of species 3 and 6 from Scheme 1 in comparison to O-phosphorylethanolamine (O-PEA).
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Figure 3: ATR-FTIR spectra of species involved in the synthesis process, from Scheme 1.
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Figure 4: SEM images of titanium anodic oxide surface with: (a,b) unmodified DND; (c,d) DND-COOH functionaliz...
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Figure 5: STEM image of immobilized aminosilanized DND 6 adsorbed to the air-formed passive layer of Ti6Al7Nb...
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