Acid- and Base-Stable Porous Organic Cages: Shape Persistence and pH Stability via Post-synthetic “Tying” of a Flexible Amine Cage
Imine cage molecules can be reduced to amines to improve their chemical stability, but this introduces molecular flexibility. Hence, amine cages tend not to exhibit permanent solid-state porosity. We report a synthetic strategy to achieve shape persistence in amine cages by tying the cage vertices w...
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| Veröffentlicht in: | Journal of the American Chemical Society 2014-05, Vol.136 (21), p.7583-7586 |
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| container_end_page | 7586 |
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| container_issue | 21 |
| container_start_page | 7583 |
| container_title | Journal of the American Chemical Society |
| container_volume | 136 |
| creator | Liu, Ming Little, Marc A Jelfs, Kim E Jones, James T. A Schmidtmann, Marc Chong, Samantha Y Hasell, Tom Cooper, Andrew I |
| description | Imine cage molecules can be reduced to amines to improve their chemical stability, but this introduces molecular flexibility. Hence, amine cages tend not to exhibit permanent solid-state porosity. We report a synthetic strategy to achieve shape persistence in amine cages by tying the cage vertices with carbonyls such as formaldehyde. Shape persistence is predicted by conformer stability calculations, providing a design basis for the strategy. The tied cages show enhanced porosity and unprecedented chemical stability toward acidic and basic conditions (pH 1.7–12.3), where many other porous crystalline solids would fail. |
| doi_str_mv | 10.1021/ja503223j |
| format | Article |
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| title | Acid- and Base-Stable Porous Organic Cages: Shape Persistence and pH Stability via Post-synthetic “Tying” of a Flexible Amine Cage |
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