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A π-stacked porphyrin-fullerene electron donor-acceptor conjugate that features a surprising frozen geometry

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  • A. Ciammaichella
  • P. Dral
  • Tim Clark
  • P. Tagliatesta
  • M. Sekita
  • D. Guldi
A “frozen” electron donor–acceptor array that bears porphyrin and fullerene units covalently linked through the ortho position of a phenyl ring and the nitrogen of a pyrrolidine ring, respectively, is reported. Electrochemical and photophysical features suggest that the chosen linkage supports both through-space and through-bond interactions. In particular, it has been found that the porphyrin singlet excited state decays within a few picoseconds by means of a photoinduced electron transfer to give the rapid formation of a long-lived charge-separated state. Density functional theory (DFT) calculations show HOMO and LUMO to be localized on the electron-donating porphyrin and the electron-accepting fullerene moiety, respectively, at this level of theory. More specifically, semiempirical molecular orbital (MO) configuration interaction (CI) and unrestricted natural orbital (UNO)-CI methods shed light on the nature of the charge-transfer states and emphasize the importance of the close proximity of donor and acceptor for effective electron transfer.
Original languageEnglish
Pages (from-to)14008-14016
Number of pages9
JournalChemistry
Volume18
Issue number44
DOIs
Publication statusPublished - 29 Oct 2012

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