(Dibenzoylmethanato)boron difluoride derivatives containing triphenylamine moieties: a new type of electron-donor/π-acceptor system for dye-sensitized solar cells.

(Dibenzoylmethanato)boron difluoride derivatives containing triphenylamine moieties were synthesized as a new type of electron-donor/π-acceptor system. These new compounds exhibited long-wavelength absorptions in the UV/Vis spectra, and reversible oxidation and reduction waves in cyclic voltammetry experiments. Their amphoteric redox properties are based on their resonance hybrid forms, in which a positive charge is delocalized on the triphenylamine moieties and a negative charge is localized on the boron atoms. Molecular orbital (MO) calculations indicate that their HOMO and LUMO energies vary with the number of phenylene rings connected to the difluoroboron-chelating ring. This is useful for optimizing the HOMO and LUMO levels to an iodine redox (I(-)/I3(-)) potential and a titanium dioxide conduction band, respectively. Dye-sensitized solar cells fabricated by using these compounds as dye sensitizers exhibited solar-to-electric power conversion efficiencies of 2.7-4.4 % under AM 1.5 solar light.