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Triptycene 1,2-Quinones and Quinols: Permeable Crystalline Redox-Active Molecular Solids

Triptycene 1,2-Quinones 和 Quinols : 可渗透的水晶的氧化还原作用活跃的分子的固体

作     者:Langis-Barsetti, Sophie Maris, Thierry Wuest, James D. 

作者机构:Univ Montreal Dept Chim Montreal PQ H3C 3J7 Canada 

出 版 物:《JOURNAL OF ORGANIC CHEMISTRY》 (有机化学杂志)

年 卷 期:2018年第83卷第24期

页      面:15426-15437页

核心收录:

学科分类:081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070303[理学-有机化学] 0703[理学-化学] 

基  金:Natural Sciences and Engineering Research Council of Canada Ministere de l'Education du Quebec Canada Foundation for Innovation Canada Research Chairs Program Universite de Montreal 

主  题:program structure oxygen STRUCTURAL STUDY open network Electrodes PERVIOUS Redox processes Crystallinity Hydroquinones benzoquinone 

摘      要:Suitably designed quinones and quinols are promising modules for the programmed construction of ordered redox-active molecular solids. To explore this potential, we have synthesized compounds 1-4, in which multiple 1,2-benzoquinone and 1,2-quinol units are attached to a triptycene core. The resulting molecules have topologies that disfavor efficient packing, and structural studies show that they crystallize to form open networks held together by characteristic attractive intermolecular forces, including O-H center dot center dot center dot O hydrogen bonds, C-H center dot center dot center dot O interactions, pi-stacking, and dipolar interactions. Remarkably, the resulting solids are permeable and can undergo reversible redox reactions without loss of crystallinity. Our work may thereby help lead to the design of robust carbon-based batteries with electrodes derived from quinones, quinols, and other redox-active molecules abundantly produced by nature.

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