Chiral Recognition of Carboxylate Anions by (R)-BINOL-Based Macrocyclic Receptors

Tyszka-Gumkowska, Agata; Pikus, Grzegorz; Jurczak, Janusz

doi:10.3390/molecules24142635

Cited by 7 publications

(3 citation statements)

References 28 publications

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“…A number of BINOLbased chiral fluorescence sensors have been exploited because of their unique luminescent properties [40,41]. Recently, a variety of new BINOL-based macrocycles emerged [42][43][44][45][46]. Anzenbacher and Ema et al reported [42] a class of macrocyclic hosts composed of chiral binaphthalene and hydrogen bond donors to recognize chiral carboxylic acids.…”

Section: Binol-based Macrocyclementioning

confidence: 99%

“…Quantitative and semiquantitative experimental results showed that the sensors 27−30 can accurately determine enantiomer excess in the solution with errors < 1.6%. In addition, (R)-BINOL-based macrocycles without the conjugated groups were synthesized to recognize chiral carboxylic acids [43]. By calculating the inclusion constants as a judgment of chiral recognition ability, the macrocycles' cavity size and appropriate geometry were demonstrated to play an important role in effective enantiomer recognition.…”

Section: Binol-based Macrocyclementioning

confidence: 99%

See 1 more Smart Citation

Advances in Chirality Sensing with Macrocyclic Molecules

Liang

Jin

et al. 2021

Chemosensors

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The construction of chemical sensors that can distinguish molecular chirality has attracted increasing attention in recent years due to the significance of chiral organic molecules and the importance of detecting their absolute configuration and chiroptical purity. The supramolecular chirality sensing strategy has shown promising potential due to its advantages of high throughput, sensitivity, and fast chirality detection. This review focuses on chirality sensors based on macrocyclic compounds. Macrocyclic chirality sensors usually have inherent complexing ability towards certain chiral guests, which combined with the signal output components, could offer many unique advantages/properties compared to traditional chiral sensors. Chirality sensing based on macrocyclic sensors has shown rapid progress in recent years. This review summarizes recent advances in chirality sensing based on both achiral and chiral macrocyclic compounds, especially newly emerged macrocyclic molecules.

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Section: Binol-based Macrocyclementioning

confidence: 99%

Section: Binol-based Macrocyclementioning

confidence: 99%

Advances in Chirality Sensing with Macrocyclic Molecules

Liang

Jin

et al. 2021

Chemosensors

View full text Add to dashboard Cite

show abstract

“…Searching for efficient pathways to obtain macrocyclic compounds, which can find applications in supramolecular chemistry as molecular receptors, , sensors, − and catalysts, − is one of the main topics of our long-term research. We previously developed two synthetic procedures addressing this problem: macrocyclization under high-pressure conditions via double quaternization of diamines by α,ω-diiodide compounds − and via double amidation of dimethyl esters by α,ω-diamines…”

Section: Introductionmentioning

confidence: 99%

Static Combinatorial Chemistry: A High-Pressure Approach to the Synthesis of Macrocyclic Benzoamide Libraries

2020

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We investigated the yield and distribution of macrocyclic products formed in combinatorial libraries (CLs) obtained via double-amidation reactions of methyl diesters with α,ω-diamines. The application of the static combinatorial chemistry (SCC) approach allowed us to generate a large number of macrocyclic diamides and tetraamides in single experiments. We show that high-pressure conditions accelerate the macrocyclization process but also have a great impact on the distribution of macrocyclic products in the presented libraries, promoting the formation of macrocyclic compounds and eliminating the linear ones. The distribution of macrocyclic products was also found to be strongly dependent on the structural features of the substrates employed. Furthermore, in three- and four-substrate CLs we observed the formation of a new type of hybrid tetraamides consisting of three different components.

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Chiral Macrocycle‐Enabled Counteranion Trapping for Boosting Highly Efficient and Enantioselective Catalysis

et al. 2020

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The tight binding enabled by tailor‐made macrocycles can be manipulated for tuning the catalysis process. In parallel to well‐developed crown ether‐based cation‐binding catalysis, a macrocycle‐enabled counteranion trapping strategy is presented for boosting highly efficient and enantioselective catalysis. A set of bis‐diarylthiourea macrocycles containing two BINOL moieties were designed and synthesized. They possess a well‐confined chiral cavity and strong binding affinities towards disulfonate anions. Caused by the tight binding, just 1 mol % macrocycle in combination with 1 mol % ethanedisulfonic acid can promote excellent conversion and up to 99 % ee in the Friedel–Crafts reaction of indoles with imines. The acid or the macrocycle alone do not afford any reactivity. The high catalytic efficiency and excellent stereocontrol was ascribed to large, complexation‐induced acidity enhancement and tight ion‐pairing facilitated by cave‐like macrocyclic cavity.

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Chiral Recognition of Carboxylate Anions by (R)-BINOL-Based Macrocyclic Receptors

Cited by 7 publications

References 28 publications

Advances in Chirality Sensing with Macrocyclic Molecules

Advances in Chirality Sensing with Macrocyclic Molecules

Static Combinatorial Chemistry: A High-Pressure Approach to the Synthesis of Macrocyclic Benzoamide Libraries

Chiral Macrocycle‐Enabled Counteranion Trapping for Boosting Highly Efficient and Enantioselective Catalysis

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