Isolation and Structural Characterization of Regioisomers of Dibrominated Terrylene Diimides

Diverse applications of rylenediimides
are attributed to the accessibility
of simple methodologies to obtain versatile halogenated precursors.
Terrylene diimides are important molecular platforms to achieve materials
with NIR absorption and emission. In this work, we present a simple
synthesis for the hitherto unknown di- and tribromo-TDIs. Regioisomerically
pure dibromo TDIs, including an elusive 1,14-derivative, could be
successfully isolated and structurally characterized along with tribromo-TDI.
The utility of these bromo derivatives has also been demonstrated
with a redox anchoring.

苝二酰亚胺（rylene diimides）的多样化应用，得益于可通过简便合成方法获取多功能卤化前驱体。三亚苝二酰亚胺（terrylene diimides，简称TDIs）是制备具备近红外（NIR）吸收与发射特性材料的重要分子平台。本研究针对此前尚未见报道的二溴代与三溴代TDIs开发了一种简便合成路线，成功分离得到区域异构体纯的二溴代TDIs（包括难以获取的1,14-位取代衍生物）与三溴代TDI，并完成了其结构表征。我们还通过氧化还原锚定实验验证了这类溴代衍生物的应用价值。