Efficient Triarylamine–Perylene Dye-Sensitized Solar Cells: Influence of Triple-Bond Insertion on Charge Recombination

We synthesize two new metal-free donor-acceptor organic dyes (C266 and C267) featuring a N-annulated perylene block. Owing to the improved coplanarity of conjugated units as well as the prolonged conjugation upon inserting a triple bond between the triarylamine and perylene segments, the C267 dye exhibits a slightly red-shifted absorption peak and an enhanced maximum molar absorption coefficient with respect to its reference dye C266, leading to an improved photocurrent output in dye-sensitized solar cells. However, the triple-bond introduction also brings forth an over 100 mV reduced open-circuit photovoltage owing to faster interfacial charge recombination, which presents a clear correlation with a reduced mean thickness of self-assembled dye layer on titania as revealed by X-ray reflectivity measurements. The C266 dye, albeit with a relatively weaker light-harvesting capacity, displays a higher power conversion efficiency of 9.0% under the 100 mW cm(-2), simulated AM1.5G sunlight.