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Hydrolysis Rate of Functionalized Fullerenes Bearing Alkoxysilanes: A Comparative Study
Author(s) -
Bianco Alberto,
Maggini Michele,
Nogarole Marco,
Scorrano Gianfranco
Publication year - 2006
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200600084
Subject(s) - chemistry , fullerene , hydrolysis , alkoxy group , reagent , sol gel , derivative (finance) , substrate (aquarium) , polymer chemistry , organic chemistry , chemical engineering , alkyl , oceanography , financial economics , engineering , economics , geology
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 1 H NMR spectroscopy by following the disappearance of selected resonances of the fullerene substrate under the conditions (HCl/H 2 O/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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)