Synthesis and Self-Assembly Behavior of Double Ullazine-Based Polycyclic Aromatic Hydrocarbons
Synthesis and Self-Assembly Behavior of Double Ullazine-Based Polycyclic Aromatic Hydrocarbons
复制标题
双芥子嗪基多环芳烃的合成及自组装行为
DOI：
10.1055/a-1472-6852
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发表时间：
2021
影响因子：
--
通讯作者：
X. Feng
中科院分区：
文献类型：
--
作者：
M. Richter;M. Borkowski;E. Dmitrieva;A. A. Popov;T. Marszalek;W. Pisula;X. Feng
多环芳香甲亚胺叶立德（PAMY，1）是自下而上合成含氮多环芳烃（N-PAH）的多功能结构单元。虽然PAMY的化学性质在几年前就已经建立，但迄今为止还没有报道过双PAMY结构单元的环加成。在这项工作中，我们证明了PAMY-二聚体（6）的第一次环加成，这打开了三种不同的烷基酯取代的N-PAH与横向延伸的双乌拉嗪支架（DU-1，DU-2和DU-3）。有趣的是，DU-1- 3的循环伏安法显示出三个可逆的氧化波，这证实了双乌拉嗪支架的富电子性质。此外，在现场光谱电化学研究乙基己基酯取代的DU-3揭示了不同的阳离子物种的形成与新的吸收带高达1689 nm。此外，通过偏光显微镜和掠入射广角X射线散射研究了所连接的取代基对薄膜形成和超分子组织的影响。
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-substitutedN-PAHs with a laterally extended double ullazine scaffold (DU-1,DU-2andDU-3). Interestingly, the cyclic voltammetry ofDU-1–3exhibited three reversible oxidation waves, which confirmed the electron-rich nature of the double ullazine scaffold. Furthermore, in situ spectroelectrochemistry study of ethylhexyl ester-substitutedDU-3revealed 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 was investigated by polarized optical microscopy and grazing incidence wide-angle X-ray scattering.