Intramolecular imine photocyclization has been explored for grafting on the bay region of perylenediimide (PDI) different electro- and photoactive chromophores to achieve new AzaBenzannulated-PDI (AzaBPDI) dyads. Triphenylamine (TPA), fluorene (Fl), perylenemonoimide (PMI), and perylenediimide (PDI) units have been successfully assembled to AzaBPDI using this straightforward one-pot synthesis starting from the easily accessible 1-aminoPDI. This original procedure was compared to the well-known Pictet–Spengler reaction and appears to be an attractive alternative in terms of versatility and efficiency with higher yields obtained. The optical and electrochemical properties of these molecular systems demonstrated large absorption capabilities in the visible range, good accepting abilities with low LUMO levels, and efficient electronic interactions between chromophoric units such as energy or electron transfers. In addition, with their large dihedral angle estimated by theoretical calculations, those dyads should present interesting applications in various organic optoelectronic devices. In particular, the PMI-AzaBPDI and PDI-AzaBPDI dyads presenting low LUMO levels, a broad absorption in the visible range, and a twisted conformation make them good candidates as non-fullerene acceptors in organic solar cells.

中文翻译：

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可见光介导的基于氮杂苯并环化的di二酰亚胺的光收集染料的合成。

已经开发了分子内亚胺光环化技术，用于在per二酰亚胺（PDI）的海湾区域上接枝不同的电活性和光活性生色团，以实现新的氮杂苯并环化的PDI（AzaBPDI）二联体。三苯胺（TPA），芴（F1），per单酰亚胺（PMI）和per二酰亚胺（PDI）单元已使用这种简单易用的一锅合成方法成功地组装成AzaBPDI，从容易获得的1-aminoPDI开始。将该原始程序与著名的Pictet-Spengler反应进行了比较，并且在多功能性和效率方面，具有较高的收率，似乎是一个有吸引力的替代方法。这些分子系统的光学和电化学性质显示出在可见光范围内的大吸收能力，低LUMO含量的良好接受能力，发色单元之间的有效电子相互作用，例如能量或电子转移。另外，由于通过理论计算估计了它们的大二面角，所以这些二元组应该在各种有机光电器件中呈现出有趣的应用。特别是，PMI-AzaBPDI和PDI-AzaBPDI二元组具有低LUMO水平，可见光范围内的宽吸收性以及扭曲的构象，使其成为有机太阳能电池中非富勒烯受体的良好候选者。