Mimicking photosynthetic antenna-reaction-center complexes with a (Boron Dipyrromethene)3-Porphyrin-C60 pentad

Jian Yong Liu, Mohamed E. El-Khouly, Shunichi Fukuzumi, Dennis K.P. Ng

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A highly efficient functional mimic of the photosynthetic antenna-reaction-center complexes has been designed and synthesized. The model contains a zinc(II) porphyrin (ZnP) core, which is connected to three boron dipyrromethene (BDP) units by click chemistry, and to a C60 moiety using the Prato procedure. The compound has been characterized using various spectroscopic methods. The intramolecular photoinduced processes of this pentad have also been studied in detail with steady-state and time-resolved absorption and emission spectroscopic methods, both in polar benzonitrile and nonpolar toluene. The BDP units serve as the antennae, which upon excitation undergo singlet-singlet energy transfer to the porphyrin core. This is then followed by an efficient electron transfer to the C60 moiety, resulting in the formation of the singlet charge-separated state (BDP)3-ZnP .+-C60.-, which has a lifetime of 476 and 1000a ps in benzonitrile and toluene, respectively. Interestingly, a slow charge-recombination process (κT CR=2.6×106a s-1) and a long-lived triplet charge-separated state (τTCS=385 ns) were detected in polar benzonitrile by nanosecond transient measurements. Good combination! Covalent linkage of three boron dipyrromethene units, a zinc(II) porphyrin core, and a C60 moiety results in the formation of a novel pentad (see figure) which can mimic the efficient processes of energy transfer followed by electron transfer occurring in photosynthetic antenna-reaction-center complexes.

Original languageEnglish
Pages (from-to)1605-1613
Number of pages9
JournalChemistry - A European Journal
Issue number5
StatePublished - 1 Feb 2011


  • boron dipyrromethenes
  • electron transfer
  • fullerenes
  • photosynthesis
  • porphyrins


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