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US 10,766,911 B2Granted
Coordinative alignment of molecules in chiral metal-organic frameworks
AssigneeThe Regents of the University of California
InventorsSeungkyu Lee, Eugene A. Kapustin, Omar M. Yaghi
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Abstract
Coordinative alignment uses x-ray diffraction to precisely and unambiguously determine the structure of molecules bound or crystallized within chiral metal organic frameworks.
Claims9
A method of coordinative alignment (CAL) to determine the structure of target molecules, comprising coordinative aligning and crystalizing the target molecules within a chiral metal organic framework (MOF), wherein:
- (i) the target molecules bind to the interior of the MOF through covalent and/or ionic bonds, and are oriented in pores of the MOF such that reduced vibrations and restricted orientations by the bonds enable structural determination of the oriented target molecules by diffraction methods like single crystal x-ray diffraction;
- (ii) chiral symmetry of the MOF serves as a reference for determining the absolute configuration of the bound target molecules, such that the chiral environment of the pore enables enantioselective crystallization of the target molecules in the pores, which can be applied to crystallize one enantiomer from a recemic mixture;
- (iii) the MOF provides sufficiently large single crystals so that the crystals diffract enough for the structure determination, and functionalities that can interact with incoming molecules, including open metal sites and organic functional groups, sufficient to make the covalent and/or ionic bonds with incoming target molecules;
- and
- (iv) the target molecules are chiral, are of size to be bound within the pores of the MOF, and comprise organic functional groups sufficient to make the covalent and/or ionic bonds with the MOF,
- wherein the functional groups of the target molecules are selected from carboxylic acid, primary alcohol, and phenol.
3 more elements
A method of coordinative alignment (CAL) to determine the structure of target molecules, comprising coordinative aligning and crystalizing the target molecules within a chiral metal organic framework (MOF), wherein:
- (i) the target molecules bind to the interior of the MOF through covalent and/or ionic bonds, and are oriented in pores of the MOF such that reduced vibrations and restricted orientations by the bonds enable structural determination of the oriented target molecules by diffraction methods like single crystal x-ray diffraction;
- (ii) chiral symmetry of the MOF serves as a reference for determining the absolute configuration of the bound target molecules, such that the chiral environment of the pore enables enantioselective crystallization of the target molecules in the pores, which can be applied to crystallize one enantiomer from a recemic mixture;
- (iii) the MOF provides sufficiently large single crystals so that the crystals diffract enough for the structure determination, and functionalities that can interact with incoming molecules, including open metal sites and organic functional groups, sufficient to make the covalent and/or ionic bonds with incoming target molecules;
- and
- (iv) the target molecules are chiral, are of size to be bound within the pores of the MOF, and comprise organic functional groups sufficient to make the covalent and/or ionic bonds with the MOF,
- wherein the target molecules are selected from:
- benzoic acid, methanol, ethylene glycol, 3-nitrophenol, heptanoic acid, 3-hydroxybenzoic acid, 3,5-diaminobenzoic acid, trimesic acid, 4-bromophenol, 2-(2,6-dichloranilino)phenylacetic acid (diclofenac), 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one (genistein), tert-butyloxycarbonyl-(RS)-3-amino-1,2-propanediol, gibberellin form A1 and A3, and (±)-jasmonic acid.
4 more elements
A method of coordinative alignment (CAL) to determine the structure of target molecules, comprising coordinative aligning and crystalizing the target molecules within a chiral metal organic framework (MOF), wherein:
- (i) the target molecules bind to the interior of the MOF through covalent and/or ionic bonds, and are oriented in pores of the MOF such that reduced vibrations and restricted orientations by the bonds enable structural determination of the oriented target molecules by diffraction methods like single crystal x-ray diffraction;
- (ii) chiral symmetry of the MOF serves as a reference for determining the absolute configuration of the bound target molecules, such that the chiral environment of the pore enables enantioselective crystallization of the target molecules in the pores, which can be applied to crystallize one enantiomer from a recemic mixture;
- (iii) the MOF provides sufficiently large single crystals so that the crystals diffract enough for the structure determination, and functionalities that can interact with incoming molecules, including open metal sites and organic functional groups, sufficient to make the covalent and/or ionic bonds with incoming target molecules;
- and
- (iv) the target molecules are chiral, are of size to be bound within the pores of the MOF, and comprise organic functional groups sufficient to make the covalent and/or ionic bonds with the MOF,
- wherein the MOF is selected from:
- a) MOF-74, MOF-808, PCN-700, MOF-545, and MOF-535;
- b) chiral MOF-5 and MOFs based on mandelate;
- and
- c) MOF-520, Al8(μ-OH)8(HCOO)4(BTB)4, (BTB=1,3,5-benzenetribenzoate).
7 more elements
Dependencies are inferred from the claim text.