Synthesis and photophysical characterization of porphyrin, chlorin and bacteriochlorin molecules bearing tethers for surface attachment

Chinnasamy Muthiah, Masahiko Taniguchi, Han-Je Kim, Izabela Schmidt, Hooi Ling Kee, Dewey Holten, David F Bocian, Jonathan S Lindsey
Photochemistry and Photobiology 2007, 83 (6): 1513-28
The ability to tailor synthetic porphyrin, chlorin and bacteriochlorin molecules holds promise for diverse studies in artificial photosynthesis. Toward this goal, the synthesis and photophysical characterization of five tetrapyrrole compounds is described. Each compound bears a surface attachment group. One set contains three meso-substituted porphyrins that differ only in the nature of a surface-binding tether-isophthalic acid, ethynylisophthalic acid or cyanoacrylic acid. The other set includes a porphyrin, chlorin and bacteriochlorin each of which bears an ethynylisophthalic acid tether. The ester derivative of each compound was prepared for solution photophysical characterization studies. The photophysical studies include determination (in toluene or acetonitrile) of the electronic absorption and fluorescence spectra, fluorescence yield and lifetime of the lowest excited singlet state. The excited-state lifetimes range from 1 to 5.6 ns for the five compounds. The radiative rate constant for the excited-state decay was estimated from the photophysical data (fluorescence yield and excited-state lifetime) and from Strickler-Berg analysis of the absorption and fluorescence spectra. The synthesis and characterization of the tetrapyrrole compounds underpin their use as sensitizers in molecular-based solar cells.

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