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T1 - Soot-free synthesis of C60

Chad Maschinot was born and raised outside of Cincinnati, OH in Crestview Hills, KY. In 2009, he pursued a Bachelor’s of Science in Chemistry at Northern Kentucky University with the plan to go onto pharmacy school. While at NKU, his interest in research grew while studying inorganic synthesis and photochemistry on C60 fullerene-transition metal systems. His research experience and personal interests in medicine led Chad to pursue a Ph. D. in medicinal chemistry. Upon completion of his B.S. in 2013, Chad enrolled in the Pharmaceutical Sciences department at the University of Connecticut. He is a 3rd year graduate student currently working towards a Ph.D. in the Hadden Lab with a focus on the synthesis and evaluation of vitamin D3 analogues as Hh pathway inhibitors with anti-cancer potential and the identification and characterization of novel cellular targets of vitamin D3 and calcitriol.

Fig. 8 Formation of a fulleroid via addition of diazomethane to C60.

Endohedral complexes of fullerenes are composed of one or more atoms inside of a carbon shell. Such species are commonly denoted as ”M@C60,” meaning atom M inside C60.[37,38] There is very little free space inside of a fullerene, so only individual atoms or small groups of atoms can be accommodated.

Endohedral fullerene - Wikipedia

1. Kroto HW, Heath JR, O'Brien SC. . C60: Buckminsterfullerene.  1985;318:162-3

P. "?Dielectric Properties of C60 and Sc3N@C80 Fullerenol Containing Polyurethane Nanocomposites"," , 2014.

Windham, A.D.; Lowe, P.M.; Conley, K.W.; Netchaev, A.D.; Buchanan, R.K.; Buchanan, J.P.. "Controlled Thiol-ene Polymer Microsphere Production using a Low-Frequency Acoustic Excitation Coaxial Flow Method," , 2016.

Stevenson, S.; Coumbe, C.E.; Mackey, M.A.; Confait, B.S.; Phillips, J.P.; Dorn, H.C; Ling, Y.; Zhang, Y.. "Preferential encapsulation and stability of La3N cluster in 80 atom cages: experimental synthesis and computational investigation of La3N@C79N," , v.131, 2009, p.

Higher fullerenes (C70 and larger fullerenes) have received much less attention than has C60.[40,41] The limited availability and high price of these molecules have made it difficult to undertake extensive studies of their chemistry. Thankfully, the reactivity of the higher fullerenes is very similar to that of C60. However, because C70 and the higher fullerenes are less symmetrical than C60, there are more options for the site of the first addition, for the second addition, and so on. Hirsch-Bingel reactions on C70 have been used to identify the most reactive site, the second reactive site, and so on.[42] As expected, the most reactive site on C70 is the C=C bond between the most pyramidalized carbons in the molecule. The second most reactive site is typically at the opposite pole of the molecule. The last to react are usually the carbons closest to the equator.

7-13 Synthesis and spectroscopic study of fluorinated fullerene, ..

Synthetic Approaches to a Variety of Covalently Linked Porphyrin-Fullerene Hybrids J.

N2 - A new synthetic medium for the production of C60 has been found that does not produce soot. C60 was produced in the liquid phase of an aerosol of precursor soot at 700 °C. The precursor soot aerosol, a high temperature stable form of hydrocarbon, was produced by pyrolysis of acetylene at atmospheric pressure in a flow tube reactor. At 700 °C, the effluent particles were found to contain PAHs, small hydrocarbons and fullerenes but no observable black material. However, when the reactor temperature was changed to 800 °C, soot was also produced in the effluent particles along with PAHs and other small hydrocarbons, and the fullerene product disappeared. These results show a clear competition between the production of fullerenes and other forms of carbon. The filter-collected effluent was shown to be completely soluble in conventional solvents suggesting the possibility of an efficient cyclic synthetic process. Fullerenes were only found in the particle phase implying the first observed liquid phase synthesis of C60.

AB - A new synthetic medium for the production of C60 has been found that does not produce soot. C60 was produced in the liquid phase of an aerosol of precursor soot at 700 °C. The precursor soot aerosol, a high temperature stable form of hydrocarbon, was produced by pyrolysis of acetylene at atmospheric pressure in a flow tube reactor. At 700 °C, the effluent particles were found to contain PAHs, small hydrocarbons and fullerenes but no observable black material. However, when the reactor temperature was changed to 800 °C, soot was also produced in the effluent particles along with PAHs and other small hydrocarbons, and the fullerene product disappeared. These results show a clear competition between the production of fullerenes and other forms of carbon. The filter-collected effluent was shown to be completely soluble in conventional solvents suggesting the possibility of an efficient cyclic synthetic process. Fullerenes were only found in the particle phase implying the first observed liquid phase synthesis of C60.

Synthesis and Photophysics of a Novel Porphyrin-C60 Hybrid, Tetrahedron Lett.
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Synthesis of C60-End-Capped Polymers ..

Fullerenes are hollow clusters of carbon atoms. The name fullerene is a shortened form of buckminsterfullerene, a name that pays homage to the designer of the geodesic dome.a The structure of C60 is reminiscent of that famous dome, being a near-perfect sphere formed from a set of fused rings in the same manner as a soccer ball. C70 is similar, having the same general structure with an extra ”belt” of 10 carbon atoms. Common members of this class of structures include C60, C70, C76, and C84, although small amounts of larger structures (”higher fullerenes”) are formed along with the more common species. As the number of carbon atoms increases, the number of possible structures increases, and indeed multiple isomers of several of the higher fullerenes have been observed.b New fullerene species have been prepared from other fullerenes, albeit in low yield.c

Annealing C60+: Synthesis of Fullerenes and Large …

The C60 cage (Ih symmetry) measures 7 A across. The C70 ”rugbyball” shape (D5h symmetry) is 7 A across and 10 A long. These highly curved structures place carbon in a strained geometry. Trivalent carbon (sp2 hybridization) typically leads to a planar geometry. In fullerenes, the bonding arrangement at carbon is far from planar—the three bonds form a shallow pyramid.[4'5] The strain in C60 is significant (over 400 kcal/mol) and is responsible for much of the reactivity of fullerenes.

Preparation and characterization of fullerene (C60) ..

A new synthetic medium for the production of C60 has been found that does not produce soot. C60 was produced in the liquid phase of an aerosol of precursor soot at 700 °C. The precursor soot aerosol, a high temperature stable form of hydrocarbon, was produced by pyrolysis of acetylene at atmospheric pressure in a flow tube reactor. At 700 °C, the effluent particles were found to contain PAHs, small hydrocarbons and fullerenes but no observable black material. However, when the reactor temperature was changed to 800 °C, soot was also produced in the effluent particles along with PAHs and other small hydrocarbons, and the fullerene product disappeared. These results show a clear competition between the production of fullerenes and other forms of carbon. The filter-collected effluent was shown to be completely soluble in conventional solvents suggesting the possibility of an efficient cyclic synthetic process. Fullerenes were only found in the particle phase implying the first observed liquid phase synthesis of C60.

Combustion synthesis of fullerenes | Request PDF

Only the pattern of a bonds is shown in Figs. 1 and 2. There is an extensive (and critically important) set of p bonds that involves every carbon atom in the molecule. It is clear from the reactivity of C60 as well as from theory that these bonds are not localized between pairs of carbon atoms, but are instead delocalized over the surface of the fullerene cage. There is some debate over whether fullerenes can be properly classified as aromatic.[7] Aromaticity is normally associated with significant electronic ring currents, diminished reactivity, and diminished bond length alternation. Fullerenes display a degree of bond length alternation. The bonds that form the fusion of a 6-membered ring with a 5-membered ring are somewhat longer (bond length of 1.46 A) than the bonds that form the fusion of two 6-membered rings (1.40 A), but this amount of bond length alternation is also found in some molecules commonly considered to be aromatic (Fig. 3).

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