BIS FULLEROPYRROLIDINE-DIBENZO18CROWN-6 CONJUGATE: CATION-COMPLEXATION INDUCED REDUCTION POTENTIAL CHANGES

摘要

A one-step synthesis of bis-pyrrolidine functionalized fullerene-dibenzo[18]crown-6 conjugate by the reaction of G_(60), sarcosine, and octahydro-hexaoxa-dibenzo(A,J) cyclooctadecene-2,13-dicarboxaldehyde is described. Elucidation of the different geometric isomers of the fullerene-dibenzo[18]crown-6 conjugate, 1, was performed by ab initio energy minimization calculations. The alkali and alkaline earth metal complexation of the conjugates was studied by ESI-mass spectroscopic methods. Cyclic voltammetric studies of the G_(60)-crown ether conjugates in the presence of metal ions revealed anodic shifts of up to 40 mV for the first and second fullerene-centered reduction processes due to the electrostatic effects of the metal ions of the crown entity that are in close proximity to the C_(60) spheroid.