| We report the first synthesis of a well-characterized “Teflon ponytail” fullerene adducts via the Hirsch-Bingel reaction with a malonate bearing two perfluorinated alkyl chains. Out of 3 different adducts synthesized, C3 tris-adduct shows excellent solubility in perfluorinated solvents, such as FC-72 and FC-75. It was found to be an efficient sensitizer for singlet oxygen formation in fluorous media, which has potential in biphasic systems and in photobiology.; In attempts to develop Fluorous/Organic phase transport systems, several approaches were investigated.; Reversible solubilization of Fullerene (C60) in fluorous media by Diels-Alder addition to perfluoroalkylated 1,3-cyclopentadiene was shown to be an unsuitable system, because the Diels-Alder addition of the fluorous diene was accompanied by extensive oxidation of the fullerene core, as revealed by MALDI-TOF data.; Perfluoroalkyl substituted α and β-cyclodextrins were synthesized and characterized. Host-guest properties of fluorous cyclodextrins synthesized were investigated in fluorous and mixed fluorous/organic media. The ability of fluorous cyclodextrins to complex small solvent molecules, perfluorocarbon chains and an azo-dye (4,4′-dihydroxyazobenzene) at homogeneous conditions was revealed. However, biphasic extraction of organic substrates by fluorous cyclodextrins from organic into fluorous phase has not been yet achieved. |
