Wild Martin, Griebel Jan, Hajduk Anna, Friedrich Dirk, Stark Annegret, Abel Bernd, Siefermann Katrin R
Department of Chemistry, Leibniz Institute of Surface Modification (IOM), Permoserstraße 15, 04318 Leipzig, Germany.
Wilhelm-Ostwald-Institute for Physical and Theoretical Chemistry, University Leipzig, Linnéstraße 2, 04103 Leipzig, Germany.
Sci Rep. 2016 May 19;6:26263. doi: 10.1038/srep26263.
The class of triarylamine-based dyes has proven great potential as efficient light absorbers in inverse (p-type) dye sensitized solar cells (DSSCs). However, detailed investigation and further improvement of p-type DSSCs is strongly hindered by the fact that available synthesis routes of triarylamine-based dyes are inefficient and particularly demanding with regard to time and costs. Here, we report on an efficient synthesis strategy for triarylamine-based dyes for p-type DSSCs. A protocol for the synthesis of the dye-precursor (4-(bis(4-bromophenyl)amino)benzoic acid) is presented along with its X-ray crystal structure. The dye precursor is obtained from the commercially available 4(diphenylamino)benzaldehyde in a yield of 87% and serves as a starting point for the synthesis of various triarylamine-based dyes. Starting from the precursor we further describe a synthesis protocol for the dye 4-{bis[4'-(2,2-dicyanovinyl)-[1,1'-biphenyl]-4-yl]amino}benzoic acid (also known as dye P4) in a yield of 74%. All synthesis steps are characterized by high yields and high purities without the need for laborious purification steps and thus fulfill essential requirements for scale-up.
基于三芳基胺的染料类别已被证明在反向（p型）染料敏化太阳能电池（DSSC）中作为高效光吸收剂具有巨大潜力。然而，p型DSSC的详细研究和进一步改进受到以下事实的严重阻碍：基于三芳基胺的染料的现有合成路线效率低下，并且在时间和成本方面要求特别高。在此，我们报告了一种用于p型DSSC的基于三芳基胺的染料的高效合成策略。给出了染料前体（4-（双（4-溴苯基）氨基）苯甲酸）的合成方案及其X射线晶体结构。该染料前体由市售的4-（二苯胺基）苯甲醛以87%的产率获得，并作为合成各种基于三芳基胺的染料的起点。从该前体出发，我们进一步描述了染料4-{双[4'-（2,2-二氰基乙烯基）-[1,1'-联苯]-4-基]氨基}苯甲酸（也称为染料P4）的合成方案，产率为74%。所有合成步骤均具有高产率和高纯度的特点，无需繁琐的纯化步骤，因此满足了放大生产的基本要求。
