Photoinduced energy and electron transfer in phenylethynyl-bridged zinc porphyrin-oligothienylenevinylene-C 60 ensembles

Maxence Urbani, Kei Ohkubo, D. M.Shafiqul Islam, Shunichi Fukuzumi, Fernando Langa

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22 Scopus citations


Donor-bridge-acceptor triad (Por-2TV-C 60) and tetrad molecules ((Por) 2-2TV-C 60), which incorporated C 60 and one or two porphyrin molecules that were covalently linked through a phenylethynyl-oligothienylenevinylene bridge, were synthesized. Their photodynamics were investigated by fluorescence measurements, and by femto- and nanosecond laser flash photolysis. First, photoinduced energy transfer from the porphyrin to the C 60 moiety occurred rather than electron transfer, followed by electron transfer from the oligothienylenevinylene to the singlet excited state of the C 60 moiety to produce the radical cation of oligothienylenevinylene and the radical anion of C 60. Then, back-electron transfer occurred to afford the triplet excited state of the oligothienylenevinylene moiety rather than the ground state. Thus, the porphyrin units in (Por)-2TV-C 60 and (Por) 2-2TV-C 60 acted as efficient photosensitizers for the charge separation between oligothienylenevinylene and C 60.

Original languageEnglish
Pages (from-to)7473-7485
Number of pages13
JournalChemistry - A European Journal
Issue number24
StatePublished - 11 Jun 2012

Bibliographical note

Funding Information:
I would like to thank R. L. Cifelli, N. J Czaplewski, L. Vitt, G. Schnell, and C. Harper for helpful comments and discussion on this project. M. Caldwell, D. Winkler, and an anonymous reviewer provided useful comments on an earlier manuscript, which substantially improved this work. S. Madsen prepared the type specimen and C. McCallister prepared Figure 1. My gratitude also goes to all the personnel at KU, UALVP, and UMMZ for their assistance during my use of their collections. Financial support was provided by the American Federation of Mineralogical Societies, Dinamation International Society (Ying Chang Scholarship) Sigma Xi, the Graduate Student Sen- ate of the University of Oklahoma, the Department of Zoology of the University of Oklahoma as well as by National Geo-graphic Society Grants 4762-91 and 5021-92 and National Science Foundation grant DEB 9401094 to R. L. Cifelli.


  • electron transfer
  • energy transfer
  • fullerenes
  • oligothienylenevinylene
  • porphyrins
  • zinc


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