Tuning charge transfer energetics in reaction center mimics via T h-functionalization of fullerenes

Fabian Spänig, Christian Kovacs, Frank Hauke, Kei Ohkubo, Shunichi Fukuzumi, Dirk M. Guldi, Andreas Hirsch

Research output: Contribution to journalArticlepeer-review

47 Scopus citations


We have introduced an approach of mono- and hexakis-adducts of C 60 involving a Th-symmetrical addition pattern, where up to 12 ferrocene or 10 ferrocene and one porphyrin units are linked flexibly to C60 with the objective to systematically raise the energy of the radical ion pair state. A detailed electrochemical and photophysical investigation has shed light onto charge transfer events that depend largely on (i) the functionalization pattern of C60, (ii) the donor strength of the donor, (iii) the excited-state energy of the predominant chromophore, and (iv) the solvent polarity. Considering (i)-(iv), the presence of the porphyrins is key to providing sufficient driving forces for affording spatially separated radical ion pair states. An ideal scenario, that is, testing ZnP-C 60-(Fc)10 (19) in benzonitrile and DMF, allows storing nearly 1.7 eV in a nanosecond lived radical ion pair state. In this context, the flexible linkage, powering a through space charge transfer, prevents, however, stabilization of the radical ion pair state beyond nanoseconds.

Original languageEnglish
Pages (from-to)8180-8195
Number of pages16
JournalJournal of the American Chemical Society
Issue number23
StatePublished - 17 Jun 2009


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