Photoinduced electron transfer in branched bis(ferrocenylacetylene)-C 60 systems: Influence of the nature of conjugation

Laura Pérez, D. M.Shafiqul Islam, Yasuyuki Araki, Pilar De La Cruz, François Cardinali, Osamu Ito, Fernando Langa

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Four new branched 3,4- and 3,5-bis(ferrocenylacetylene)-phenyl-C 60 molcules, in which the bis-ferrocene donor moieties and C 60 acceptor moiety are covalently linked with phenylacetylene linkage through pyrrolidino and pyrazolino rings on the C60 moiety, as abbreviated to be (Fc)2≡Ph-NMPC60 (o- and m-) and (Fc)2≡Ph-PzC60 (o- and m-), respectively, have been prepared in multistep procedures using microwave irradiation, as source of energy. The HOMO-LUMO gaps smaller than 1.25 eV were experimentally determined by cyclic voltammetry (CV) and Osteryoung square-wave voltammetry (OSWV) for (Fc)2≡Ph-PzC60 and (Fc)2≡Ph- NMPC60. In both polar and non-polar solvents, a photoinduced charge-separation (CS) process efficiently takes place in (Fc) 2≡Ph-NMPC60 and (Fc)2≡Ph-PzC 60 from the singlet excited state of C60 ( 1C60*), as confirmed by picosecond-time-resolved emission spectroscopy. The CS states were confirmed by nanosecond-transient absorption spectroscopy. The lifetimes of the CS states were evaluated to be ca. 10 ns, which are shorter than those of the similar dyads with phenylenevinylene linkage, suggesting higher electron-hole conductivity through the phenylacetylene linkage.

Original languageEnglish
Pages (from-to)3535-3543
Number of pages9
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
Publication statusPublished - 2008 Jul 1

Keywords

  • Electron transfer
  • Fullerenes
  • Metallocenes

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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