[60]Fullerene-porphyrin-ferrocene triad self-assembled monolayers (SAMs) for photovoltaic applications

초록

A new triad array, C-60-triosmium cluster-zinc porphyrin-ferrocene complex 1, Os(3)C(60)ZnPFc, was prepared by the decarbonylation of Os-3(CO)(9)(mu(3)-eta(2):eta(2):eta(2)-C-60) (9) and subsequent reaction with an isocyanide ligand containing porphyrin and ferrocene. This novel triad array exhibits well-defined and stable electrochemical properties in solution due to a robust bonding mode between the C-60 and the triosmium cluster. Compound 2, Os(3)C(60)SiZnPFc was prepared in a manner similar to that of compound 1 from Os-3(CO)(8)(CN(CH2)(3)Si(OEt)(3))(mu(3)-eta(2):eta(2):eta(2)-C-60) (10) and an isocyanide ligand containing porphyrin and ferrocene. The SAM of triad 2 (2/ITO) was fabricated by immersion of an ITO electrode into a chlorobenzene solution of 2 and diazabicyclooctane (2:1 equiv.), and characterized by UV-Vis absorption spectroscopy and cyclic voltammetry. The triad SAM exhibited ideal, well-defined electrochemical responses and high stability due to the stable C-60 pi-delocalized system via a linkage with the metal cluster center as well as a robust bonding mode. The photoelectrochemical properties of the 2/ITO triad were investigated by a standard three-electrode system in the presence of an ascorbic acid sacrificial electron donor. Reproducible photocurrent was generated by excitation of the porphyrin moiety in the triad SAM with visible light. (C) 2014 Elsevier B.V. All rights reserved.

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