Two-dimensional X-shaped organic dyes bearing two anchoring groups to TiO2 photoanode for efficient dye-sensitized solar cells

Novel two-dimensional X-shaped donor–π–acceptor (D–π–A)-type dyes were designed and successfully synthesized for use in a dye-sensitized solar cell (DSSC). Two triphenylamine units in these dyes act as electron donor units, while two cyanoacrylic acid groups act as electron acceptor units and anchoring groups to the TiO2 photoanode. The photovoltaic properties of the newly synthesized dye-containing DSSCs were investigated to identify the effects of conjugation length between the electron donors and acceptors, and the molecular energy levels of the dyes. Among the three dyes we synthesized, (2E,2′E)-3,3′-(5′,5″-(4,5-bis(4-(bis(4-tert-butylphenyl)amino)styryl)-1,2-phenylene)bis(2,2′-bithiophene-5′,5-diyl))bis(2-cyanoacrylic acid) (11) showed the highest power conversion efficiency of 3.14% (ηmax = 4.06% with TiCl4 treatment) under AM 1.5G illumination (100 mW cm−2) in a photoactive area of 0.418 cm2 with short circuit current density of 7.27 mA cm−2, open circuit photovoltage of 612 mV, and a fill factor of 70.6%.

► New organic photosensitizing dyes have been synthesized.
► High molecular extinction coefficients were obtained.
► Two-dimensional shape of the molecule is beneficial for light harvesting.
► One of three dyes showed the PCE of 3.14% in DSSC.