Elucidation of Diverse Solid‐State Packing in a Family of Electron‐Deficient Expanded Helicenes via Microcrystal Electron Diffraction (MicroED)**
| Autor: | Harrison M. Bergman, Julia Oktawiec, T. Don Tilley, Adrian E. Samkian, Hosea M. Nelson, Gavin R. Kiel, Christopher G. Jones |
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| Rok vydání: | 2020 |
| Předmět: |
Materials science
010405 organic chemistry Resolution (electron density) Space group General Medicine General Chemistry 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences law.invention Crystal Crystallography chemistry.chemical_compound Helicene chemistry Electron diffraction law Self-assembly Homochirality Crystallization Single crystal Divergent synthesis |
| Zdroj: | Angewandte Chemie International Edition. 60:2493-2499 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.202012213 |
| Popis: | Solid-state packing plays a defining role in the properties of a molecular organic material, but it is difficult to elucidate in the absence of single crystals that are suitable for X-ray diffraction. Here, we demonstrate the coupling of divergent synthesis with microcrystal electron diffraction (MicroED) for rapid assessment of solid-state packing motifs, using a class of chiral nanocarbons – expanded helicenes – as a proof of concept. Two highly selective oxidative dearomatizations of a readily-accessible helicene provided a divergent route to four electron-deficient analogues containing quinone or quinoxaline units. Crystallization efforts consistently yielded microcrystals that were unsuitable for single crystal X-ray diffraction, but ideal for MicroED. This technique facilitated the elucidation of solid-state structures of all five compounds with |
| Databáze: | OpenAIRE |
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