Preparative-Scale Separation of Enantiomers Using Intercalated .alpha.-Zirconium Phosphate

Garcia, Maurie E.; Naffin, Jacqueline L.; Deng, Nanlin; Mallouk, Thomas E.

doi:10.1021/cm00058a030

Cited by 43 publications

(34 citation statements)

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“…In 1995, Mallouk et al 49 pioneered optical resolution of amine (1,2-diaminocyclohexane, 85% ee) through intercalation by a layered phosphate with an optically active building block. In 2001, Lin et al 50 reported resolution of racemic 1,2-diaminocyclohexane (13.6% and 10% ee for (S,S)-and (R,R)-1,2-diaminocyclohexane, respectively) on a flash chromatography using chiral laminar lanthanide phosphonates of BINOL as solid phases.…”

Section: Synthesis and Characterization Of The Mofsmentioning

confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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The separation of racemic molecules is of substantial significance not only for basic science but also for technical applications, such as fine chemicals and drug development. Here we report two isostructural chiral metal-organic frameworks decorated with chiral dihydroxy or -methoxy auxiliares from enantiopure tetracarboxylate-bridging ligands of 1,1 0 -biphenol and a manganese carboxylate chain. The framework bearing dihydroxy groups functions as a solid-state host capable of adsorbing and separating mixtures of a range of chiral aromatic and aliphatic amines, with high enantioselectivity. The host material can be readily recycled and reused without any apparent loss of performance. The utility of the present adsorption separation is demonstrated in the large-scale resolution of racemic 1-phenylethylamine. Control experiments and molecular simulations suggest that the chiral recognition and separation are attributed to the different orientations and specific binding energies of the enantiomers in the microenvironment of the framework.

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Section: Synthesis and Characterization Of The Mofsmentioning

confidence: 99%

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

et al. 2014

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“…The specific host-guest interactions in such solids are important in a variety of areas such as electrochemistry, separation science, catalysis and chemical/bio sensing [2][3][4]. The phenomenon of molecular recognition has been demonstrated in layered compounds like clays, metal phosphates, phosphonates and layered double hydroxides (LDHs) [5,6].…”

Section: Introductionmentioning

confidence: 99%

Near 100% selectivity in anion exchange reactions of layered zinc hydroxy nitrate

Thomas¹,

Rajamathi²

2011

Journal of Colloid and Interface Science

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“…The design of porous solids that can selectively and reversibly bind molecules has been the subject of much recent interest. [1] These highly specific interactions are critical in a range of important practical chemical technologies such as chemical sensing, [2±4] separations, [5] and catalysis [6] . The design of lamellar inorganic hosts such as clays, phosphates, phosphonates and modified thin films that exhibit molecular recognition features has recently been reviewed by Mallouk and Gavin.…”

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confidence: 99%

New Separation Science Using Shape-Selective Ion Exchange Intercalation Chemistry

et al. 1999

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Optical Absorption and Photoluminescence (PL) Measurements: The LiPBO sample was prepared as a thin film on a quartz substrate by thermal evaporation at a rate of 0.2 /s at 5´10 ±6 torr. Optical absorption and PL spectra were measured by UV-vis spectrometry and IAE-PL-SYS-1 (Nanotech) equipped with a linear charge coupled device detector (Ocean Optics, S2000) and a Xenon lamp coupled with a monochromator. For the PL measurements, the excitation wavelength was fixed as 365 nm, with regard to the absorption spectrum.Fabrication and Characteristics of OELD: A 1:1 mixture of poly(ether imide) (PEI) and N,N¢-diphenyl-N,N¢-bis(3-methylphenyl)-[1,1¢-diphenyl]-4,4¢-diamine (TPD) were dissolved in chloroform to form a solution concentration of ca. 0.5 wt.-%. The solution was spun for ca. 1.5 min at 5000 rpm onto ITO glass, which had a seven-segment pattern on it, and subsequently dried at 110 C for ca. 1 h. The dried polyimide HTL film had a thickness of 375 as determined by a surface profiler (Tencor P-10). Next, LiPBO was thermally evaporated onto the polyimide HTL using a low-temperature effusion cell (EPI-30-M-LT). The evaporation rate, the temperature, the vacuum, and the film thickness were ca. 0.1 /s, 315 C, 5´10 ±6 torr, and 200 , respectively. A 3500 thick layer of Aluminum was deposited on the LiP-BO thin film by thermal evaporation at a rate of up to 5 /s. The evaporation rate and thickness were detected using a thickness monitor (Sycon Instruments STM-100/MF). The luminance±current density±voltage (L±J±V) characteristics of OELD were measured by IAE-OELD-SYS with an electrometer (Keithley 237), a calibrated photodiode, a diode array rapid scan analyzer (PSI DARSA-2000), and a candela meter (Minolta CS1000). The electroluminescent (EL) spectra were measured by a spectrophotometer (JOBIN-YVON-SPEX 270M) with a photomultiplier tube (PMT) as a detector and the IAE-PL-SYS-1 mentioned previously.The design of porous solids that can selectively and reversibly bind molecules has been the subject of much recent interest. [1] These highly specific interactions are critical in a range of important practical chemical technologies such as chemical sensing, [2±4] separations, [5] and catalysis [6] . The design of lamellar inorganic hosts such as clays, phosphates, phosphonates and modified thin films that exhibit molecular recognition features has recently been reviewed by Mallouk and Gavin. [7] In lamellar inorganic solids, guest molecules access intracrystalline binding sites via intercalation reactions. In most cases, inorganic intercalation reactions are unselective processes which are driven by either oxidation±reduction, ion-exchange, acid±base, or donor±acceptor reactions. The interlamellar gallery expands to accommodate the guest species resulting in little size-or shape-selectivity to the reaction. Here we report the use of a crystalline-ordered layered double hydroxide (LDH) that exhibits shape-selective intercalation. In addition, we have found that this remarkable shape selectivity can be controlled by alterin...

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Preparative-Scale Separation of Enantiomers Using Intercalated .alpha.-Zirconium Phosphate

Cited by 43 publications

References 0 publications

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Engineering chiral porous metal-organic frameworks for enantioselective adsorption and separation

Near 100% selectivity in anion exchange reactions of layered zinc hydroxy nitrate

New Separation Science Using Shape-Selective Ion Exchange Intercalation Chemistry

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