Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials**
Squarephaneic Tetraanhydride: A Conjugated Square-Shaped Cyclophane for the Synthesis of Porous Organic Materials**
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方烷四酐：用于合成多孔有机材料的共轭方形环烷**
DOI：
10.1002/ange.202212623
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发表时间：
2022
影响因子：
--
通讯作者：
Eder S
中科院分区：
文献类型：
--
作者：
Eder S
芳族羧酸酐是有机材料化学中普遍存在的结构单元，并且在有机半导体、颜料和电池电极材料的合成中受到相当大的关注。在这里，我们扩展了家庭的芳香族羧酸酐与一个独特的新成员，共轭环番与四个酸酐基团。环蕃在三步合成中获得，并且可以有效地官能化，如通过转化成四酰亚胺和八羧酸酯所示。晶体结构揭示了新结构单元可实现的高孔隙度。优异的电化学性能和可逆还原的四阴离子的酰亚胺; NMR和EPR测量证实了全球芳香性的二阴离子和证据的全球贝尔德芳香性的四阴离子。考虑到合成时间短和独特的性质，我们期望这种新的结构单元在有机材料的开发中得到广泛的应用。
Aromatic carboxylic anhydrides are ubiquitous building blocks in organic materials chemistry and have received considerable attention in the synthesis of organic semiconductors, pigments, and battery electrode materials. Here we extend the family of aromatic carboxylic anhydrides with a unique new member, a conjugated cyclophane with four anhydride groups. The cyclophane is obtained in a three‐step synthesis and can be functionalised efficiently, as shown by the conversion into tetraimides and an octacarboxylate. Crystal structures reveal the high degree of porosity achievable with the new building block. Excellent electrochemical properties and reversible reduction to the tetraanions are shown for the imides; NMR and EPR measurements confirm the global aromaticity of the dianions and evidence the global Baird aromaticity of the tetraanions. Considering the short synthesis and unique properties, we expect widespread use of the new building block in the development of organic materials.