Soluble fulleropyrrolidines bearing a trialkoxysilyl functionality (methoxy, ethoxy, butoxy, and isopropoxy) have been prepared and characterized. The hydrolysis rate constant for each fulleropyrrolidine was measured with 1H NMR spectroscopy by following the disappearance of selected resonances of the fullerene substrate under the conditions (HCl/H2O/THF) used for the preparation of fullerene-doped sol–gel glasses. It has been found that fulleropyrrolidine 1, bearing the trimethoxysilyl group, hydrolyzes faster than substrates 2–7 and should be the reagent of choice to minimize aggregation of the fullerene spheroid in sol–gel glassy matrices. The triethoxysilyl derivative 2, our benchmark fulleropyrrolidine for incorporation in sol–gel glasses, has the secondfastest hydrolysis rate.
Hydrolysis rate of functionalized fullerenes bearing alkoxysilanes: A comparative study
MAGGINI, MICHELE;SCORRANO, GIANFRANCO
2006
Abstract
Soluble fulleropyrrolidines bearing a trialkoxysilyl functionality (methoxy, ethoxy, butoxy, and isopropoxy) have been prepared and characterized. The hydrolysis rate constant for each fulleropyrrolidine was measured with 1H NMR spectroscopy by following the disappearance of selected resonances of the fullerene substrate under the conditions (HCl/H2O/THF) used for the preparation of fullerene-doped sol–gel glasses. It has been found that fulleropyrrolidine 1, bearing the trimethoxysilyl group, hydrolyzes faster than substrates 2–7 and should be the reagent of choice to minimize aggregation of the fullerene spheroid in sol–gel glassy matrices. The triethoxysilyl derivative 2, our benchmark fulleropyrrolidine for incorporation in sol–gel glasses, has the secondfastest hydrolysis rate.
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