1,8-Diazabicycloundecene-mediated Separation of Singly Bonded Fullerene Dimer and Application to Facile Preparation of C₆₁H₂

Abstract

We investigated the complexation of a singly bonded fullerene dimer [C₆₀(CH₂SiMe₂OⁱPr)]₂ and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in order to develop facile separation of a fullerene derivative from the mixture of fullerene and its derivatives without the use of time consuming and expensive chromatographic techniques. Addition of DBU to a 1,2,4-trimethylbenzene (TMB) solution of C₆₀ and [C₆₀(CH₂SiMe₂OⁱPr)]₂ afforded complexation only with [C₆₀(CH₂SiMe₂OⁱPr)]₂, leading to precipitation of the [C₆₀(CH₂SiMe₂OⁱPr)]₂-DBU complex. Decomplexation with 1,2-dichlorobenzene gave [C₆₀(CH₂SiMe₂OⁱPr)]₂ in 56% recovery. In addition, the [C₆₀(CH₂SiMe₂OⁱPr)]₂-DBU complex could be used for the synthesis of dihydromethano[60]fullerene C₆₁H₂.

Keywords:

• fullerene
• diazabicycloundecene
• charge transfer complex
• separation
• extraction

Additional information

Funding

This research is granted by the Japan Society for the Promotion of Science (JSPS) through the “Funding Program for Next Generation World-Leading Researchers (NEXT Program),” initiated by the Council for Science and Technology Policy (CSTP).