Synthesis and photophysical properties of a pyrazolino[60]fullerene with dimethylaniline connected by an acetylene linkage

Andreas Gouloumis, Frédéric Oswald, Mohamed E. El-Khouly, Fernando Langa, Yasuyuki Araki, Osamu Ito

Research output: Contribution to journalArticlepeer-review

12 Citations (Scopus)

Abstract

A new triad based on pyrazolino[60]fullerene and a conjugated dimethylaniline group has been synthesized by a copper-free Sonogashira cross-coupling reaction using microwave irradiation as the source of energy. The electrochemical and photophysical properties of the triad were systematically investigated by techniques such as time-resolved fluorescence and transient absorption spectroscopy. Charge separation via the excited singlet state of the C60 moiety was confirmed in polar and nonpolar solvents and competes with triplet formation of the C60 moiety. The charge-separated state persisted for 91 ns. Such long lifetimes are characteristic of long distances between the radical anion of the pyrazolino[60]fullerene derivative and the radical cation of the dimethylaniline moiety.

Original languageEnglish
Pages (from-to)2344-2351
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
Publication statusPublished - 2006 May 12

Keywords

  • Electron transfer
  • Fullerenes
  • Microwave irradiation
  • Photophysical properties

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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