Structure-Performance Correlations of Organic Dyes with an Electron-Deficient Diphenylquinoxaline Moiety for Dye-Sensitized Solar Cells

The high performances of dye-sensitized solar cells (DSSCs) based on seven new dyes are disclosed. Herein, the synthesis and electrochemical and photophysical properties of a series of intentionally designed dipolar organic dyes and their application in DSSCs are reported. The molecular structures of the seven organic dyes are composed of a triphenylamine group as an electron donor, a cyanoacrylic acid as an electron acceptor, and an electron-deficient diphenylquinoxaline moiety integrated in the p-conjugated spacer between the electron donor and acceptor moieties. The DSSCs based on the dye DJ104 gave the best overall cell performance of 8.06%; the efficiency of the DSSC based on the standard N719 dye under the same experimental conditions was 8.82 %. The spectral coverage of incident photon-to-electron conversion efficiencies extends to the onset at the near-infrared region due to strong internal charge-transfer transition as well as the effect of electron-deficient diphenylquinoxaline to lower the energy gap in these organic dyes. A combined tetraphenyl segment as a hydrophobic barrier in these organic dyes effectively slows down the charge recombination from TiO2 to the electrolyte and boosts the photovoltage, comparable to their Ru-II counterparts. Detailed spectroscopic studies have revealed the dye structure-cell performance correlations, to allow future design of efficient light-harvesting organic dyes.