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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DOI：
10.1002/anie.202212623
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发表时间：
2022-11-25
影响因子：
16.6
通讯作者：
Glocklhofer, Florian
中科院分区：
文献类型：
--
作者：
Eder, Simon;Ding, Bowen;Thornton, Daisy B.;Sammut, Darlene;White, Andrew J. P.;Plasser, Felix;Stephens, Ifan E. L.;Heeney, Martin;Mezzavilla, Stefano;Glocklhofer, Florian
芳香族羧酸酐是有机材料化学中普遍存在的组成单元，在有机半导体、颜料和电池电极材料的合成中受到了极大的关注。在这里，我们用一个独特的新成员--具有四个酸酐基团的共轭环番--扩展了芳香族羧酸酐的家族。环番是通过三步合成得到的，并且可以有效地官能化，如转化为四亚胺和八羧酸盐所示。晶体结构显示了新的积木可实现的高度多孔性。亚胺类化合物表现出优异的电化学性质和可逆还原为四阴离子；核磁共振和电子顺磁共振测试证实了二阴离子的全局芳香性，并证明了四阴离子的全局Baird芳香性。考虑到合成时间短和独特的性质，我们期待着这种新的构建块在有机材料的开发中得到广泛的应用。介绍了芳香族羧酸酐构筑块家族中的一个独特的新成员--具有四个酸酐基团的共轭方形环番。构建块可以通过三步合成获得，并有效地官能化，以获得从高孔隙率到优异的电化学性能的高度有趣的性能，如转化为亚胺和羧酸盐所显示的。
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. A unique new member of the family of aromatic carboxylic anhydride building blocks—a conjugated square‐shaped cyclophane with four anhydride groups—is presented. The building block can be obtained in a three‐step synthesis and functionalised efficiently to give materials with highly interesting properties ranging from high degrees of porosity to excellent electrochemical properties, as shown by the conversion into imides and carboxylates.
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影响因子：
3.6
作者：
Alvey, Paul M.;Reczek, Joseph J.;Lynch, Vincent;Iverson, Brent L.
通讯作者：
Iverson, Brent L.
大孔结晶聚酰亚胺共价有机骨架的设计合成
影响因子：
16.6
作者：
Fang, Qianrong;Zhuang, Zhongbin;Yan, Yushan
通讯作者：
Yan, Yushan
DOI：
10.1107/s0567740878006901
发表时间：
1978-01-01
期刊：
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE
影响因子：
--
作者：
LJUNGSTROM, E;LINDQVIST, O;WENNERSTROM, O
通讯作者：
WENNERSTROM, O
影响因子：
16.6
作者：
Maschita, Johannes;Banerjee, Tanmay;Lotsch, Bettina, V
通讯作者：
Lotsch, Bettina, V
影响因子：
--
作者：
HEADGORDON, M;GRANA, AM;WHITE, CA
通讯作者：
WHITE, CA