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The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

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Abstract

A strategy that leverages solvent effects to noncovalently trap solid and unstable liquid organic compounds within a crystalline sponge ({[(ZnI2)3(tris(4-pyridyl)-1,3,5-triazine)2x(CHCl3)}n) 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 tert-butyl ether (MTBE) solvent was demonstrated by trapping (E)-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 (E)-stilbene. Trapping of vanillin and (+)-artemisinin elicited single-crystal-to-single-crystal transformations where space group symmetry reduced from C2/c to P[1 with combining macron] and C2, respectively, and the absolute configuration of (+)-artemisinin was determined through anomalous dispersion.

Graphical abstract: The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

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Publication details

The article was received on 10 May 2017, accepted on 13 Jul 2017 and first published on 14 Jul 2017


Article type: Paper
DOI: 10.1039/C7CE00885F
Citation: CrystEngComm, 2017, Advance Article
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    The crystalline sponge method: a solvent-based strategy to facilitate noncovalent ordered trapping of solid and liquid organic compounds

    T. R. Ramadhar, S. Zheng, Y. Chen and J. Clardy, CrystEngComm, 2017, Advance Article , DOI: 10.1039/C7CE00885F

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