Electron transfer in nonpolar solvents in fullerodendrimers with peripheral ferrocene units

Chemistry. 2006 Jun 23;12(19):5149-57. doi: 10.1002/chem.200600207.

Abstract

Two new fullerodendrimers, with two and four ferrocene units on their periphery, have been synthesized by 1,3-dipolar cycloaddition reactions between the corresponding azomethine ylides and C(60). These new compounds have been studied by using cyclic voltammetry and UV/Vis spectroscopy. Weak intramolecular interactions between the fullerene cage and the ferrocene groups have been found. The photochemical events of both fullerene-ferrocene dendrimers have been probed by means of steady-state and time-resolved techniques. The steady-state emission intensities of the fulleropyrrolidine-ferrocene dendrimers 1 and 2 were found to be quenched relative to the N-methylfulleropyrrolidine without substituents that was used as a model. The nanosecond transient absorption spectral studies revealed efficient charge separation in both systems, even in toluene. The lifetimes of the (C(60))(*-)-(dendron)(*+) are higher for the second-generation fullerodendrimer (with four ferrocene units) and they are of the order of tens of nanoseconds in toluene and hundreds of nanoseconds in polar solvents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Electrochemistry
  • Ferrous Compounds / chemistry*
  • Fullerenes / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Metallocenes
  • Solvents
  • Spectrometry, Fluorescence
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Spectrophotometry, Infrared
  • Spectrophotometry, Ultraviolet
  • Thermodynamics

Substances

  • Ferrous Compounds
  • Fullerenes
  • Indicators and Reagents
  • Metallocenes
  • Solvents
  • ferrocene