DMSO: An Efficient Catalyst for the Cyclopropanation of C_60, C₇₀, SWNTs, and Graphene through the Bingel Reaction

Abstract

Dimethyl sulfoxide (DMSO) with sodium carbonate (Na2CO3) is an effective catalyst system for C60 cyclopropanation through the Bingel reaction. Various bromomalonic esters, brominated β-keto esters, brominated 1,3-diketones, and other bromo-substituted active methylene compounds can react with C60 in the presence of DMSO and Na2CO3 to achieve excellent yields of the corresponding methanofullerenes at 10 °C. Moreover, this proposed methodology has been also employed successfully to functionalize [70]­fullerene, single-walled carbon nanotubes (SWNTs), and graphene. This protocol is beneficial because it involves short reaction time, high yield, and a simple procedure. Additionally, this method does not need a strong base, such as sodium hydride and 1,8-diazabicyclo­[5,4,0]­undec-7-ene, because inexpensive Na2CO3 can be the catalyst.

Methanofullerene Synthesis via Photogenerated Fullerene Radical Anion Intermediates

“…In contrast, when the incandescent lamp was used, the reaction was slow; however, no decrease in the yield of 2d was observed. This photochemical reaction using diethyl 2,2-dibromomalonate 1e as a starting material gave 2e in a good yield, comparable to the previously reported Bingel reaction . The reaction of C 60 with dibromodimedone 1f gave fullerene derivative 3 instead of methanofullerene 2f in a moderate yield.…”

Repurposing of oxazolone chemistry: gaining access to functionalized graphene nanosheets in a top-down approach from graphite

“…9,10 The most employed approaches for graphene modication involve the chemistry of graphene oxide 11 (GO), especially esterication/amidation reactions at the carboxylic groups and the coupling of diazonium salts to the sp 2 network. 12,13 Other important approaches to fabricate functionalized graphene materials are 1,3-dipolar cycloaddition (1,3-DC), 14,15 the Bingel reaction, 16 the Diels-Alder reaction (DA), 17,18 among others, 19,20 which directly take place on the graphene surface. These synthetic strategies are not devoid of drawbacks due to the low intrinsic reactivity of graphene, which is lower than that of other carbon nanoforms such as fullerene and carbon nanotubes, principally because of the absence of tension in the graphene basal planes.…”

Fullerenes for rechargeable battery applications: Recent developments and future perspectives

“…Therefore, in future research will require a systematic performance evaluation, including capacity retention, Coulombic efficiency, and rate performance. Developing suitable methods to prepare fullerene-based materials on a large scale is also helpful to its practical application [94]. Finally, detailed performance comparisons between fullerenebased materials and other carbon materials are required to reasonably evaluate their application prospects.…”