Cyclodextrin‐Functionalised Nanomaterials for Enantiomeric Recognition

Hobbs, Christopher; Řezanka, Pavel; Řezanka, Michal

doi:10.1002/cplu.202000187

Cited by 10 publications

(3 citation statements)

References 137 publications

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“…Modification of oxide surfaces and particles by organic ligands has numerous applications, such as in selective separations, chemical sensing, selective catalysis, and drug delivery. − A common feature of these applications is a dependence on chemical and physical interactions between an analyte and a recognition site, referred to as the “molecular recognition event”. The molecular recognition event is sensitive to the chemical composition, local structure, and, where relevant, chirality of the organic modifier. ,− Therefore, it is of great importance to understand the properties of organic modifiers when immobilized onto surfaces.…”

Section: Introductionmentioning

confidence: 88%

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂

et al. 2022

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Organic ligands grafted to oxide surfaces are used for sensing, chromatography media, catalysis, and area-selective atomic layer deposition. Beyond simply occupying space, the structure of the grafted ligands provides an opportunity to encode information onto surfaces. However, as the ligands become more complex than simple alkanes, it is not always clear how much of their structure is retained upon grafting. Here, chiral 1,1′-bi-2-naphthol (BINOL) and related BINOLates are supported onto TiO 2 and Al 2 O 3 . The molecular structure and orientation of BINOL was probed in detail utilizing surface enhanced Raman spectroscopy. BINOL on TiO 2 possesses significant in-plane (1493 cm −1 ), out of plane (785 cm −1 ), and torsional modes (427 cm −1 ), indicating naphthyl rings tilted off the perpendicular from the surface and with a dihedral angle between the two naphthyl rings of 65−80°, broadly analogous to the structure of molecular BINOL complexes. In contrast, BINOL on Al 2 O 3 has relatively fewer in-plane modes (1220 cm −1 ), in proportion to out-of-plane modes (552 cm −1 ) and torsional modes (382 cm −1 ), indicating that the naphthyl rings lie more flat with respect to the surface. BINOL on TiO 2 was further characterized by a combination of infrared, ultraviolet−visible, and circular dichroism spectroscopies to confirm that BINOL is covalently bound to TiO 2 through the phenol oxygen and that BINOL retains its chirality upon immobilization onto TiO 2 . These spectroscopies also indicate that the BINOL orientation is preserved upon atomic layer deposition of Al 2 O 3 on BINOL-TiO 2 . These results suggest strategies for the development of new functional hybrid and oxide materials.

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Section: Introductionmentioning

confidence: 88%

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂

et al. 2022

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“…Tal sucesso justifica-se devido à possibilidade das ciclodextrinas poderem ser usadas para modificar, melhorar ou controlar as propriedades dos compostos guest. Como exemplos, podemos citar o aumento da solubilidade e da biodisponibilidade de fármacos [37][38][39], a diferenciação enantiomérica [40][41][42], o controlo da volatilidade e das propriedades antioxidantes de alguns compostos [43][44][45], a modificação de parâmetros de micelização de tensioativos [46], o aumento do tempo de vida de prateleira de alimentos embalados [47] e a sua utilização em catálise [48,49].…”

Section: Ciclodextrinasunclassified

Dextrinas a Nanoesponjas: um Caminho de Êxito Trilhado pelas Ciclodextrinas

Artur J. M. Valente,

Gianluca Utzeri,

Dina Murtinho

2023

BSPQuimica

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Dextrins to Nanosponges: a Successful Path Taken by Cyclodextrins. Cyclodextrins are oligosaccharides with a wide range of applications since the last decades of the 20 th century, although their discovery occurred at the end of the 19 th century. Due to their donutlike structure and, essentially, their amphiphilic characteristics, cyclodextrins make it possible to modify the physicochemical properties of many compounds through the formation of supramolecular complexes. One of the most common modifications is making insoluble or sparingly soluble compounds soluble in aqueous systems. With so many predicates, many other ways of using cyclodextrins have been developed. Due to the presence of hydroxyl groups on both ends of the donut, cyclodextrins allow both polymerization and their use as substituent groups in polymers or nanoparticles, among others. In recent years, methods of synthesizing cyclodextrin nanosponges have markedly developed, as they combine high surface areas with a high complexation capacity, finding numerous applications in biomedical and environmental areas. This article summarizes the path followed by cyclodextrins since their discovery.

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“…Additionally, the effective methods of surface immobilization or free chiral selectors have gained popularity in these separation techniques [26][27][28][29]. A considerable number of naturally occurring chiral selectors have been applied in commercialization so far, such as cyclodextrin and its derivatives [30][31][32][33][34], proteins [35][36][37], nanomaterials [38][39][40][41], and so forth. In terms of pharmacological activity, ofloxacin interacts directly with deoxyribonucleic acid (DNA) and synergizes with DNA gyrase.…”

Section: Introductionmentioning

confidence: 99%

Separation of ofloxacin enantiomers by capillary electrophoresis with fluorescence detection using deoxyribonucleic acid oligonucleotides as chiral selectors

Chao

Qiu

Zhou

et al. 2022

J of Separation Science

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This study used capillary electrophoresis with fluorescence detection‐ and a partial‐filling mode‐based method for chiral separation of ofloxacin. The deoxyribonucleic acid oligonucleotides with different base sequences were studied as potential chiral selectors including deoxyribonucleic acid tetrahedron, G‐quadruplex, and G‐riched double‐strand deoxyribonucleic acid. Under the optimized conditions, all the deoxyribonucleic acid chiral selectors exhibited excellent chiral separation capabilities with a resolution higher than 1.5. The electrophoretic behavior of the ofloxacin enantiomer might result from the intermediate conjugate with different stabilities between chiral selectors and analytes by a combination of the hydrogen bond and spatial recognition structure. Moreover, satisfactory repeatability regarding run‐to‐run and interday repeatability was obtained, and all the relative standard deviation values of migration times and resolutions were below 4% (n = 6). Conclusively, both spatial structure and arrangement of the G bases potentiated the chiral separation capability of deoxyribonucleic acid for ofloxacin enantiomer. This work offered a stepping stone for enantioseparation using deoxyribonucleic acid as chiral selectors.

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Cyclodextrin‐Functionalised Nanomaterials for Enantiomeric Recognition

Cited by 10 publications

References 137 publications

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂

Dextrinas a Nanoesponjas: um Caminho de Êxito Trilhado pelas Ciclodextrinas

Separation of ofloxacin enantiomers by capillary electrophoresis with fluorescence detection using deoxyribonucleic acid oligonucleotides as chiral selectors

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Cyclodextrin‐Functionalised Nanomaterials for Enantiomeric Recognition

Cited by 10 publications

References 137 publications

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO2

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO2

Dextrinas a Nanoesponjas: um Caminho de Êxito Trilhado pelas Ciclodextrinas

Separation of ofloxacin enantiomers by capillary electrophoresis with fluorescence detection using deoxyribonucleic acid oligonucleotides as chiral selectors

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Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂

Orientation of 1,1′-Bi-2-naphthol Grafted onto TiO₂