Polycyclic aromatic azomethine ylides (PAMY, 1) are versatile building blocks for the bottom-up synthesis of nitrogen-containing polycyclic aromatic hydrocarbons (N-PAHs). Although the chemistry of PAMY was already established few years ago, the cycloaddition of a double PAMY building block has not been reported so far. In this work, we demonstrate the first cycloaddition of a PAMY-dimer (6), which opens the access to three different alkyl ester-substituted N-PAHs with a laterally extended double ullazine scaffold (DU-1, DU-2 and DU-3). Interestingly, the cyclic voltammetry of DU-1-3 exhibited three reversible oxidation waves, which confirmed the electron-rich nature of the double ullazine scaffold. Furthermore, in-situ spectroelectrochemistry study of ethylhexyl ester-substituted DU-3 revealed the formation of different cationic species with new absorption bands up to 1689 nm. Additionally, the influence of the attached substituents on the film formation and supramolecular organization in the thin films were investigated by polarized optical microscopy and grazing incidence wide-angle X-ray scattering.

中文翻译：

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双Ullazine基多环芳烃的合成及自组装行为

多环芳基偶氮甲亚胺（PAMY，1）是自底向上合成含氮多环芳烃（N-PAHs）的通用构建基块。尽管几年前已经建立了PAMY的化学结构，但迄今为止尚未见到双PAMY结构单元的环加成反应。在这项工作中，我们证明了PAMY-二聚体（6）的第一次环加成反应，它打开了通过侧向延伸的双ullazine支架（DU-1，DU-2和DU- 3）。有趣的是，DU-1-3的循环伏安法展示了三个可逆的氧化波，这证实了双ullazine支架的富电子性质。此外，乙基己基酯取代的DU-3的原位光谱电化学研究表明，形成了不同的阳离子物种，并具有高达1689 nm的新吸收带。另外，通过偏振光学显微镜和掠入射入射广角X射线散射研究了连接的取代基对薄膜中膜的形成和超分子组织的影响。