Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Kacprzak, Karol; Gawroński, Jacek

doi:10.1002/9783527628179.ch13

Cited by 14 publications

(15 citation statements)

References 160 publications

(127 reference statements)

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“…Selectivity of the Cinchona carbamate CSPs can inter alia be easily modulated by the modification of 6 0 position in the quinoline ring of the Cinchona moiety [15][16][17][18] or the carbamoyl group residue [15,16] (see Scheme 1). The strategy of this work was the development and evaluation of novel type of Cinchona carbamate CSP-1 comprising quinine 3,5-dinitrophenylcarbamate as a selector linked onto silica gel by 1,2,3-triazole spacer [19].…”

Section: Karol M Kacprzak 1 Wolfgang Lindnermentioning

confidence: 99%

“…On the other hand major factors responsible for the chiral discrimination of these CSPs involve, besides the long-range non-directional strong electrostatic (ion-pairing), intermolecular hydrogen bonding, Van der Waals and steric interactions [15]. The commercialized CSPs comprising tert-butylcarbamoylquinine or quinidine (ChiralPak QN-AX and Chiralpak QD-AX from Chiral Technologies) as selectors show high selectivity towards a number of acidic compounds such as: N-protected aminoacids, carboxylic, phosphonic, phosphinic and phosphoric acids, among many others [16,17].…”

Section: Introductionmentioning

confidence: 99%

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Novel Pirkle‐type quinine 3,5‐dinitrophenylcarbamate chiral stationary phase implementing click chemistry

Kacprzak

Lindner

2011

J of Separation Science

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A new Pirkle-anion exchange hybrid-type chiral stationary phase (CSP-1) has been synthesized by immobilizing 10,11-didehydroquinine 3,5-dinitrophenylcarbamate onto 3-azidopropyl silica gel using click chemistry (1,3-dipolar Huisgen cycloaddition). This chiral selector and CSP contain a strong π-accepting 3,5-dinitrophenyl residue besides the π-basic quinoline group and an ionizable tertiary amino group. In concert with ion pairing it offers π-donor-π-acceptor interactions resulting in an enhancement of the selectivity toward specific π-donating analytes such as aryloxypropionic acids and profens. A representative set of these analytes has been investigated under various chromatographic conditions (polar-organic, reversed- and normal-phase) leading to base-line enantioseparations with selectivity (α) values up to 1.8. Control experiments with related quinine tert-butylcarbamate phase grafted onto the surface either by thioether (Chiralpak QN-AX) or 1,2,3-triazole linker revealed the impact of the additional aromatic moiety in the chiral selector motif.

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Section: Karol M Kacprzak 1 Wolfgang Lindnermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel Pirkle‐type quinine 3,5‐dinitrophenylcarbamate chiral stationary phase implementing click chemistry

Kacprzak

Lindner

2011

J of Separation Science

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“…On the other hand major factors responsible for the chiral discrimination of these CSPs involve, besides the long‐range non‐directional strong electrostatic (ion‐pairing), intermolecular hydrogen bonding, Van der Waals and steric interactions 15. The commercialized CSPs comprising tert ‐butylcarbamoylquinine or quinidine (ChiralPak QN‐AX and Chiralpak QD‐AX from Chiral Technologies) as selectors show high selectivity towards a number of acidic compounds such as: N ‐protected aminoacids, carboxylic, phosphonic, phosphinic and phosphoric acids, among many others 16, 17.…”

Section: Introductionmentioning

confidence: 99%

“…Selectivity of the Cinchona carbamate CSPs can inter alia be easily modulated by the modification of 6′ position in the quinoline ring of the Cinchona moiety 15–18 or the carbamoyl group residue 15, 16 (see Scheme ). The strategy of this work was the development and evaluation of novel type of Cinchona carbamate CSP‐1 comprising quinine 3,5‐dinitrophenylcarbamate as a selector linked onto silica gel by 1,2,3‐triazole spacer 19.…”

Section: Introductionmentioning

confidence: 99%

Triple Emission from Organic/Inorganic Hybrid Nanovesicles in a Single Excitation

Narayana

Chandrasekar

2011

ChemPhysChem

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Dedicated to Professor Klaus MüllenThe fabrication of shape-defined luminescent nano/microscale objects from small molecules has attracted increasing attention among scientist owing to their unique optical and electronic properties. [1,2] Particularly, the generation of multicolor emissions from single organic and organic/inorganic hybrid nano-objects in a singlewavelength excitation is of great interest due to their potential use in solid-state lighting and color barcode applications. Until now, no reports are available on a molecularly engineered single organic or organic/inorganic nano/micro structure displaying blue-, greenand red-color triple emissions. Recently, we reported [2] the preparation of nanostructure templates self-assembled from ligand molecules and subsequently demonstrated their use by performing "coordination chemistry on the surface of the organic ligand super-structures " to generate dual-emitting (blue and red) organic/inorganic hybrid nanotubes. In our bottom-up self-assembly technique, in addition to supramolecular interactions, [3] the growth, final-shape and dimension of the nano-objects are all dependent on parameters such as: 1) molecular design, 2) solvent polarity, and 3) molecular concentration.Adopting our method, [2] we have envisioned to fabricate tricolor (blue, green and red) emitting organic/inorganic nanoobjects by single-wavelength excitation in a single pot. This goal indeed required a step-by-step approach (Scheme 1): i) careful design and synthesis of a novel dual (blue and green) emitting amphiphilic-type ligand molecule (1), ii) selection of appropriate solvent(s) for the growth of self-assembled nanostructure templates, and iii) subsequent sub-stochiometric incorporation of red luminescent Eu III metal ions on the membrane of the ligand nanostructure. Firstly, a dual-emitting (blue and green) amphiphilic ligand molecule 1 was synthesized by connecting two units of blue emitting 4-triazolyl-2,6-bispyrazoScheme 1. Schematic representation of the formation of dual-emitting (blue and green) organic nanovesicles obtained from ligand 1 and an innovative route towards triple-color-emitting (blue, green and red) hybrid organic/ inorganic nanovesicles via coordination of Eu III ions on the membrane of the ligand vesicles in THF/water. The color-coded arrows indicate the corresponding emission colors.[a] Y.

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“…[48] . These CSPs are involved in electrostatic interactions [49] . The structure of QN and QD consists of a planar quinoline and a rigid quinuclidine ring, which are connected by a secondary methyl alcohol bridge.…”

Section: Cinchona Alkaloid-based Cspsmentioning

confidence: 99%

Investigation of Novel Cinchona Alkaloid-based Zwitterionic Chiral Stationary Phases in Cation- and Zwitterion-Exchange Modes

Grecsó¹

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Resolution of Racemates and Enantioselective Analytics by Cinchona Alkaloids and Their Derivatives

Cited by 14 publications

References 160 publications

Novel Pirkle‐type quinine 3,5‐dinitrophenylcarbamate chiral stationary phase implementing click chemistry

Novel Pirkle‐type quinine 3,5‐dinitrophenylcarbamate chiral stationary phase implementing click chemistry

Triple Emission from Organic/Inorganic Hybrid Nanovesicles in a Single Excitation

Investigation of Novel Cinchona Alkaloid-based Zwitterionic Chiral Stationary Phases in Cation- and Zwitterion-Exchange Modes

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