New sonochemical reactions of the C₆₀ fullerene with amino alcohols yielding morpholine–C₆₀ adducts

Abstract

A selective and efficient method for the synthesis of previously unknown mono-adducts of the C₆₀ fullerene with fused morpholine moieties has been developed based on the reaction of C₆₀ with amino alcohols, including biogenic amines (2-aminoethanol, 2-amino-1-phenylethanol, noradrenaline, and adrenaline), in a mixed solvent (toluene/DMF) at room temperature under air and ultrasonication. The radical anion C₆₀^•‒ (g = 2.0004 and ΔH_1/2 = 3.4 G) was detected as a key intermediate by the EPR method upon the synthesis of the C₆₀–morpholine adduct. This intermediate results due to the one-electron transfer from 2-aminoethanol onto the C₆₀ core.

Keywords:

• Ultrasound
• fullerene С₆₀
• amino alcohols
• cycloaddition reaction
• radical anion C₆₀^•–

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

The structural studies of compounds were performed in “Agidel” Collective Usage Center at the Institute of Petrochemistry and Catalysis (Russian Academy of Sciences) in accordance with the Federal Program (FMRS-2022-0077 and FMRS-2022-0078). EPR spectra were recorded using the equipment of CCU “Spektr” (IMCP, UFRC of RAS).