An Enantioselective Potentiometric Sensor for 2-Amino-1-Butanol Based on Chiral Porous Organic Cage CC3-R

Wang, Bang-Jin; Aihong, Duan; Zhang, Junhui; Cao, Qiue

doi:10.3390/molecules24030420

Cited by 11 publications

(5 citation statements)

References 40 publications

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“…Analogous to enantioselective chromatography and electrophoresis, CSs can be also employed in electrochemical, optical, or mass-sensitive sensors for enantioselective detection of particular enantiomers, although the sensitivity of electrochemical sensors toward the minor enantiomeric component is still rather low. Chiral electrochemical sensors can be based on (a) CS incorporated in an electrode membrane, (b) differences in uptake of enantiomers by molecularly imprinted polymers (MIP), , and also (c) chiral doping of electrodeposited conducting polymers . Song et al developed electroactive chiral sensors for chiral amine by synthesizing binaphthol-containing electropolymers which were characterized by cyclic voltammetry, potentiometry, and in situ conductivity measurements, showing discrimination ability toward chiral amines .…”

Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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It is not a coincidence that both chirality and noncovalent interactions are ubiquitous in nature and synthetic molecular systems. Noncovalent interactivity between chiral molecules underlies enantioselective recognition as a fundamental phenomenon regulating life and human activities. Thus, noncovalent interactions represent the narrative thread of a fascinating story which goes across several disciplines of medical, chemical, physical, biological, and other natural sciences. This review has been conceived with the awareness that a modern attitude toward molecular chirality and its consequences needs to be founded on multidisciplinary approaches to disclose the molecular basis of essential enantioselective phenomena in the domain of chemical, physical, and life sciences. With the primary aim of discussing this topic in an integrated way, a comprehensive pool of rational and systematic multidisciplinary information is provided, which concerns the fundamentals of chirality, a description of noncovalent interactions, and their implications in enantioselective processes occurring in different contexts. A specific focus is devoted to enantioselection in chromatography and electromigration techniques because of their unique feature as “multistep” processes. A second motivation for writing this review is to make a clear statement about the state of the art, the tools we have at our disposal, and what is still missing to fully understand the mechanisms underlying enantioselective recognition.

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Section: Trends In Enantioselective Recognition In Natural and Synthe...mentioning

confidence: 99%

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

2022

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“…CC3–R was stable in a membrane electrode even after being treated with tetrahydrofuran or rinsed with water for 48 h, implying stability under organic solvents. The constituents of the membrane, the loading amount of CC3–R, or the pH of the environment affected its enantioselectivity, and the maximum efficiency of the CC3–R–PVC membrane electrode was achieved at a pH of 9.0 [ 89 ]. In addition to the CC3–family, CC10, one of the imine-linked POCs, also has enantiomer separation ability.…”

Section: Other Composite Membranesmentioning

confidence: 99%

Enantioselective Mixed Matrix Membranes for Chiral Resolution

2021

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Most pharmaceuticals are stereoisomers that each enantiomer shows dramatically different biological activity. Therefore, the production of optically pure chemicals through sustainable and energy-efficient technology is one of the main objectives in the pharmaceutical industry. Membrane-based separation is a continuous process performed on a large scale that uses far less energy than the conventional thermal separation process. Enantioselective polymer membranes have been developed for chiral resolution of pharmaceuticals; however, it is difficult to generate sufficient enantiomeric excess (ee) with conventional polymers. This article describes a chiral resolution strategy using a composite structure of mixed matrix membrane that employs chiral fillers. We discuss several enantioselective fillers, including metal-organic frameworks (MOFs), covalent organic frameworks (COFs), zeolites, porous organic cages (POCs), and their potential use as chiral fillers in mixed matrix membranes. State-of-the-art enantioselective mixed matrix membranes (MMMs) and the future design consideration for highly efficient enantioselective MMMs are discussed.

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“…[ 1 ] The study of chiral recognitions has received compelling attention in recent years, and therefore it is very important to understand the rational of asymmetric catalysis [ 2 ] or synthesis, [ 3 ] and the development of chiral separation [ 4 ] and sensing. [ 5 ] During the past few years, considerable effort has been devoted to the development of simple, effective and low‐cost enantioselective sensors. Among them, fluorescence (FL)‐based sensors are of interest due to their simplicity, high sensitivity, convenience, sensitivity, selectivity and low cost.…”

Section: Introducationmentioning

confidence: 99%

Porous organic cage for enantiomeric fluorescence recognition of amino acid and hydroxy acid

et al. 2021

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A new method based on the enantioselective recognition of porous organic cages CC3‐R was established for the first time. Porous organic cages are widely used for separation, adsorption and host–guest interaction sensing, but are rarely used for fluorescence sensing. Based on the inherent chiral environment of CC3‐R and the inherent fluorescence properties of the organic ligands constituting the cage, when different chiral monomers diffuse into the cage, different effects occur to produce changes in fluorescence. We found for the first time that the fluorescence of CC3‐R can be enhanced and quenched by tyrosine and mandelic acid, respectively, and that different chiral monomers are enhanced or quenched differently at the same concentration. Unlike the chiral recognition of other composite luminescent materials, the chiral porous organic cage not only utilizes its own host–guest effect for chiral recognition, but also utilizes the organic ligands constituting the cage for luminescence recognition. This work provides an alternative method to accomplish chiral recognition other than chromatography, that is using porous organic cages (POC), but it can show the advantages of simplicity, low cost and high sensitivity. We believe this work could provide valuable thoughts in the exploration of POC in chiral recognition as new FL probes for the future.

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An Enantioselective Potentiometric Sensor for 2-Amino-1-Butanol Based on Chiral Porous Organic Cage CC3-R

Cited by 11 publications

References 40 publications

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Recognition in the Domain of Molecular Chirality: From Noncovalent Interactions to Separation of Enantiomers

Enantioselective Mixed Matrix Membranes for Chiral Resolution

Porous organic cage for enantiomeric fluorescence recognition of amino acid and hydroxy acid

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