Novel D-π-A system based on zinc porphyrin dyes for dye-sensitized solar cells: Synthesis, electrochemical, and photovoltaic properties

We have designed and synthesized novel zinc porphyrin dyes which have a D-π-A system based on porphyrin derivatives containing a triphenylamine (TPA) electron-donating group and a phenyl carboxyl anchoring group substituted at the meso position of the porphyrin ring, yielding the push-pull porphyrins as the most efficient green dye for dye-sensitized solar cell (DSSC) applications. The synthesis and characterization of a novel D-π-A system based on zinc-porphyrin derivatives have been investigated through their photophysical and photoelectrochemical studies. A large red-shift of the absorption maxima due to introduction of the TPA moiety at the meso position of the porphyrin ring was expected in the D-π-A porphyrins, but the absorption maxima of HKK-Por dyes were a little red-shifted in contrast to Zn[5,-10,15-triphenyl-20-(4-carboxylphenyl)-porphyrin], due to the tilted structure between TPA and the porphyrin unit. Under the photovoltaic performance measurement, the maximum incident photon-to-current conversion efficiency (IPCE) value of the DSSC based on HKK-Por 5 was slightly higher than the efficiencies of the DSSCs based on other HKK-Por dyes due to the introduction of the alkoxy group into the TPA moiety at the meso position of the porphyrin ring. A maximum photon-to-electron conversion efficiency of 3.36% was achieved with the DSSC based on HKK-Por 5 dye (JSC = 9.04 mA/cm2, VOC = 0.57 V, FF = 0.66) under AM1.5 irradiation (100 m Wcm−2).

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Novel zinc porphyrin dyes with triphenylamine moieties was synthesized for DSSC. ► Hexyloxy-containing TPA moiety was introduced at the 15 position of the porphyrin. ► It increases the electron-donating ability of D-π-A system based on porphyrin dye. ► It also decreases the dye aggregation. ► A conversion efficiency of 3.36% was achieved with the DSSC based on HKK-Por 5 dye.