Functionalization of [60]fullerene by photoinduced electron transfer (PET): Syntheses of 1-substituted 1,2-dihydro[60]fullerenes

Siedschlag, Christina; Luftmann, Heinrich; Wolff, Christian; Mattay, Jochen

doi:10.1016/s0040-4020(97)00078-1

Cited by 43 publications

(24 citation statements)

References 16 publications

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“…Using photooxidant methodology presumed to generate transient C 60 + , reactions with ethers, aldehydes, and alcohols have been shown to produce 1,2-H(R)C 60 derivatives in modest isolated yields (Scheme 3). 447 These results are consistent with earlier analyticalscale studies by Schuster and Wilson on the addition of hydrocarbons to a derivatized C 60 cation, detected by mass spectrometry. 448 Similar multiple addition products with alcohols were originally interpreted as O-bonded adducts arising from nucleophilic addition 448 but have since been recognized as C-bonded species.…”

Section: G Fullerenium Cationssupporting

confidence: 91%

Discrete Fulleride Anions and Fullerenium Cations

2000

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His research interests include reactive cation and superacid chemistry with inert carborane counterions, ionic liquids, bioinorganic chemistry, spin-coupling phenomena, fullerene chemistry, and new carbon-or porphyrin-based materials. He is a Sloan Fellow, a Dreyfus Teacher−Scholar Awardee, and a Guggenheim Fellow. Robert Bolskar received his B.S. degree in Chemistry from Carroll College in Waukesha, WI, in 1992. He earned his Ph.D. degree at the University of Southern California in Los Angeles under the direction of Christopher Reed in 1997, investigating the synthetic redox chemistry of fullerene anions and cations. In 1998 he moved to the University of California, Riverside, as Managing Research Associate. He is currently Senior Chemist at TDA Research in Wheat Ridge, CO. His research interests include the chemistry and physics of fullerene compounds, supramolecular chemistry, strongly oxidizing systems, and electrophilic cations.

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Section: G Fullerenium Cationssupporting

confidence: 91%

Discrete Fulleride Anions and Fullerenium Cations

2000

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“…Furthermore, we also investigated additions of NMTAD to the 1-functionalized 1,2-dihydro[60]fullerenes 2 and 3, since the cis-1 bond near the hydrogen atom is not subject to any steric demand. [14] For the preparation of the addition products 4, 5 and 6, solutions of NMTAD and fullerene monoadducts 1, 2 and 3 in 1,1,2,2-tetrachloroethane were irradiated at 419 nm for 3Ϫ4 h (Scheme 1). Chromatography on silica gel afforded bis(functionalized) fullerene derivatives 4, 5 and 6 in 30, 24 and 43% yields, respectively.…”

Section: Resultsmentioning

confidence: 99%

Functionalization of [60]Fullerene and of [60]Fullerene Monoadducts by Photochemical Cycloaddition of 4‐Methyl‐1,2,4‐triazoline‐3,5‐dione

2003

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The photoreactions of 4‐methyl‐1,2,4‐triazoline‐3,5‐dione (NMTAD) with C60 and with several fullerene derivatives have been studied. In general, NMTAD cycloadds to C60 and to its monoadducts with closed structures in a highly regioselective [2+2] fashion at a cis‐1 [6,6] double bond. Cycloadditions to azafulleroids occur by a slightly different pathway and result in partially cluster‐opened bis(adducts). 1,6‐Methano[60]fulleroid, however, also undergoes a [2+2+2] cycloaddition in the absence of light. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

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“…Since the discovery of C 60 and its large scale preparation (1,2) a lot of work has been devoted to this research field (3)(4)(5) .…”

Section: Introductionmentioning

confidence: 99%