Department of Chemistry, University of Aarhus, Langelandsgade 140, DK-8000, Aarhus C, Denmark.
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100, Copenhagen Ø, Denmark.
ChemSusChem. 2023 Jun 22;16(12):e202202320. doi: 10.1002/cssc.202202320. Epub 2023 Apr 25.
One key challenge in the development of viable organic photovoltaic devices is to design component molecules that do not degrade during combined exposure to oxygen and light. Such molecules should thus remain comparatively unreactive towards singlet molecular oxygen and not act as photosensitizers for the generation of this undesirable species. Here, novel redox-active chromophores that combine these two properties are presented. By functionalizing indenofluorene-extended tetrathiafulvalenes (IF-TTFs) with cyano groups at the indenofluorene core using Pd-catalyzed cyanation reactions, we find that the reactivity of the exocyclic fulvene carbon-carbon double bonds towards singlet oxygen is considerably reduced. The new cyano-functionalized IF-TTFs were tested in non-fullerene acceptor based organic photovoltaic proof-of-principle devices, revealing enhanced device stability.
在开发可行的有机光伏器件方面，一个关键的挑战是设计在同时暴露于氧气和光的情况下不会降解的组件分子。因此，这些分子应该对单重态氧保持相对不反应，并且不作为生成这种不理想物质的光敏剂。在这里，提出了结合这两种特性的新型氧化还原活性生色团。通过使用 Pd 催化的氰化反应，在吲哚并芴扩展的四硫富瓦烯（IF-TTF）的吲哚并芴核心上用氰基官能化，我们发现，外环富烯碳-碳双键对单重态氧的反应性大大降低。新的氰基官能化 IF-TTF 被测试用于非富勒烯受体的有机光伏原理验证器件中，显示出增强的器件稳定性。
