Synthesis and Photovoltaic Performance of (Octyloxyphenyl)pyrido-[3,4-b]pyrazine-based Sensitizers for Dye-sensitized Solar Cells

doi:10.6023/A14090642

Abstract

Dye-sensitized solar cell (DSSC) is one of the promising technologies for the alternative to traditional silicon- based solar cells due to its ecological and economical fabrication processes. As one of the key components of a DSSC, the sensitizers have been demonstrated to be extremely important in determining the photoelectric conversion efficiency and device stability of DSSCs. In our previous study, a series of new pyrido[3,4-b]pyrazine-based organic sensitizers (PP-I and APP-I～IV) containing different donors and π-bridges have been synthesized and employed successfully in DSSCs. However, despite their remarkable stability, all of the devices exhibited quite low open-circuit voltages (V_ocs), which is adverse to the solar-to-electric power conversion efficiency (η). Therefore, to address this, we have replaced the 2,3-bis(4-methoxyphenyl)pyrido[3,4-b]pyrazine (APP) with 2,3-bis-(4-(octyloxy)phenyl)pyrido[3,4-b]pyrazine (OPP). As a result, a series of new sensitizers (OPP-I～Ⅲ) has been designed and synthesized with triphenylamine as the electron donor, OPP as the auxiliary acceptor, thiophene, furan and benzene as the π-linker, and cyanoacrylic acid as the acceptor moiety. Their optical and electrochemical properties, device performance and charge transfer kinetics were measured and studied. Compared with APP-Ⅲ, which has the highest V_oc in the previous work, the V_ocs of DSSCs based on OPP-I and OPP-Ⅲ have indeed been improved. Results showed that the replacement of the methoxy group with an octyloxy group can effectively reduce the π-π aggregation of the dyes on TiO₂ films. Moreover, the steric hindrance of the octyloxy group successfully suppressed charge recombination and improved the open-circuit voltage. DSSCs based on OPP-Ⅲ with benzene as the π-linker have higher V_oc than that of its counterparts with thiophene and furan as the π-linker, which might be ascribed to the bigger dihedral angle between benzene and OPP unit. In the end, DSSCs based on OPP-I showed the best conversion efficiency of 6.57% (J_sc=11.70 mA·cm^-2, V_oc=717 mV, ff=0.78) under standard global AM 1.5 solar light condition.

Key words: pyrido[3,4-b]pyrazine, octyloxybenzene, sensitizers, dye-sensitized solar cells

Cite this article

Zhang Xiaoyu, Ying Weijiang, Wu Wenjun, Li Jing, Hua Jianli. Synthesis and Photovoltaic Performance of (Octyloxyphenyl)pyrido-[3,4-b]pyrazine-based Sensitizers for Dye-sensitized Solar Cells[J]. Acta Chim. Sinica, 2015, 73(3): 272-280.

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辛氧基苯基取代的吡啶并[3,4-b]吡嗪染料的合成与光伏性能研究