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Updated: Aug 11, 2026

Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
Published on: September 26, 2016
Synthesis of fluorous fullerene adducts: reversible solubilization of fullerenes in perfluorinated solvents
Abstract:
Fullerene (C60) Diels-Alder adducts with perfluoroalkylated 1,3-cyclopentadiene (1a,b) were synthesized and studied. The perfluoroalkylated cyclopentadiene was found to be less reactive toward C60 than cyclopentadiene itself, possibly because of the electron-withdrawing effect of the side chain. Because of the same effect, the temperature of the retro-Diels-Alder reaction for the fluorinated adducts was lower (70 degrees C) than the reported value (95 degrees C) for the cyclopentadiene adducts of C60. Higher adducts of the fluorous diene and C60 were found to be soluble in perfluorohexane and to show visible partitioning between organic (toluene) and fluorous phases. Also, the Diels-Alder addition of the fluorous diene was accompanied by extensive oxidation of the fullerene core, as revealed by MALDI-TOF data.
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