The Crystalline Sponge Method: A Solvent-Based Strategy to Facilitate Noncovalent Ordered Trapping of Solid and Liquid Organic Compounds
A strategy that leverages solvent effects to noncovalently trap solid and unstable liquid organic compounds within a crystalline sponge ({[(ZnI ) (tris(4-pyridyl)-1,3,5-triazine) ]· (CHCl )} ) in a simple, mild, and efficient fashion for target molecule structure determination via X-ray diffraction...
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Veröffentlicht in: | CrystEngComm 2017, Vol.19 (31), p.4528-4534 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | A strategy that leverages solvent effects to noncovalently trap solid and unstable liquid organic compounds within a crystalline sponge ({[(ZnI
)
(tris(4-pyridyl)-1,3,5-triazine)
]·
(CHCl
)}
) in a simple, mild, and efficient fashion for target molecule structure determination via X-ray diffraction is disclosed. Host-guest structures were obtained using third-generation synchrotron radiation, and new beamline hardware allowed rapid data collection in ~5-24 minutes. This is 40-90% faster than previously reported crystalline sponge synchrotron datasets collected by us, and approximately a 150-720-fold decrease in time versus using a typical in-house diffractometer, effectively enabling the potential for high-throughput analysis. The new target molecule inclusion method using methyl
-butyl ether (MTBE) solvent was demonstrated by trapping (
)-stilbene, vanillin, 4-(trifluoromethyl)phenyl azide, and (+)-artemisinin (an antimalarial drug). The potential of guests to maximize intermolecular interactions with the crystalline sponge framework at the expense of attenuating intramolecular interactions (e.g., π-conjugation) was observed for (
)-stilbene. Trapping of vanillin and (+)-artemisinin elicited single-crystal-to-single-crystal transformations where space group symmetry reduced from
2/
to
1̄ and
2, respectively, and the absolute configuration of (+)-artemisinin was determined through anomalous dispersion. |
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ISSN: | 1466-8033 1466-8033 |
DOI: | 10.1039/c7ce00885f |