Catalysis in Cyclodextrin-Based Unconventional Reaction Media: Recent Developments and Future Opportunities

Hapiot, F.; Menuel, S.; Ferreira, Michel; Léger, B.; Bricout, H.; Tilloy, S.; Monflier, Éric

doi:10.1021/acssuschemeng.6b02886

Cited by 56 publications

(49 citation statements)

References 68 publications

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“…The four cavitands, cucurbiturils, g-cyclodextrin, sulfonatocalix [6]arene and sulfonatocalix [8]arene, have been highlighted in this review for their effectiveness to steer the reactivity of alkenes towards PCA [2 + 2]. The void spaces within the cavitands were envisioned to be useful in confining and preorienting the reactants towards PCA over the facile isomerization pathway.…”

Section: Discussionmentioning

confidence: 99%

“…The reported efficient use of cavitand-mediation approach as a general method for affecting cross-PCA [68] involves taking advantage of electronic and/or steric complementarity between the reactants and the tight space within the g-CD cavity; as two different olefins in the medium driven by hydrophobic forces compete for the cavitand's nonpolar interior, hetero guest-pair combination will be more favorable than the homo-guest pair combinations (Scheme 5) for reaction between cinnamic acids (1) and coumarins (8). The reported efficient use of cavitand-mediation approach as a general method for affecting cross-PCA [68] involves taking advantage of electronic and/or steric complementarity between the reactants and the tight space within the g-CD cavity; as two different olefins in the medium driven by hydrophobic forces compete for the cavitand's nonpolar interior, hetero guest-pair combination will be more favorable than the homo-guest pair combinations (Scheme 5) for reaction between cinnamic acids (1) and coumarins (8).…”

Section: Cross-photocycloaddition Between Cinnamic Acids and Coumarinsmentioning

confidence: 99%

“…Of the possible four isomeric dimers (Scheme 6, 15-18) irradiation of 14 resulted in 71 % Scheme 5. Cyclodextrin-influenced product distribution (in percentage) from the cross-photocycloaddition between cinnamic acids (1) and coumarins (8). Table 5.…”

Section: Pca Of Stilbazolesmentioning

confidence: 99%

“…Irradiation of stilbazoles under similar conditions in presence of half equivalent of calix [8]arene (CA8) and calix [6]arene (CA6) resulted in predominantly anti HT dimer (76 %, Table 6) and the isomerized product only, suggesting a similar alignment in the complex as well. The reactants' selfdirecting influence based on charge-repulsion is rather strong, and is mostly unaffected by the cavitand (CB8, g-CD or CAs); this is especially interesting considering that CA6 and CA8 are anionic while CB8 and g-CD are neutral.…”

Section: Pca Of Stilbazolesmentioning

confidence: 99%

“…Cavitand mediated photodimerization of alkenes has been known since the early 1980s. Like CB8 and g-CD, the octa-and hexameric members of the calixarene family (figure 1), calix [8]arene and calix [6]arene (CA8 and CA6), possesses cavity volume suitable for PCA reactions. [53] 3.…”

Section: Introductionmentioning

confidence: 99%

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Cucurbiturils as Reaction Containers for Photocycloaddition of Olefins

Pattabiraman

Sivaguru

Ramamurthy

2017

Israel Journal of Chemistry

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The [2+2] photocycloaddition (PCA [2+2]) of alkenes is one of the most synthetically useful photoreactions. It is a convenient one‐step reaction that is useful for generating substituted cyclobutanes, polymers, and biologically relevant molecules. However, the reaction efficiency is limited by its bimolecular nature requiring encounter between two reactants within the narrow window of excited state lifetime of the photoactive alkene, and competition from the unimolecular photoisomerization. Our groups have utilized macrocyclic cavitands, especially cucurbiturils(CB), to confine two alkene molecules within their cavities and steer them towards a single dimer regio‐ and stereoselectively. Although, primarily the review focuses on photocycloaddition within CBs, such reactions in closely related cavitands such as cyclodextrins (CD) and calixarenes (CA) are also briefly mentioned to provide a comparison with CBs. Studies on photocycloaddition of olefins within CB by other research groups are also briefly highlighted. A mechanistic model, with ability to predict the nature of the dimer product formed within the above reaction containers is included.

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Section: Discussionmentioning

confidence: 99%

Section: Cross-photocycloaddition Between Cinnamic Acids and Coumarinsmentioning

confidence: 99%

Section: Pca Of Stilbazolesmentioning

confidence: 99%

Section: Pca Of Stilbazolesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Cucurbiturils as Reaction Containers for Photocycloaddition of Olefins

Pattabiraman

Sivaguru

Ramamurthy

2017

Israel Journal of Chemistry

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Emission‐Tunable Room‐Temperature Phosphorescent Polymers Based on Dynamic Reversible Supramolecule‐Mediated Photocrosslinking

Lin

2021

Advanced Optical Materials

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Pure organic room‐temperature phosphorescence (RTP) materials can be used in optoelectronics, biochemical equipment, sensors and biological imaging. In the past few years, dynamic covalent chemistry has attracted significant attention because it provides a new way to produce intelligent optical materials with feedback functions. Two polymers are synthesized through supramolecular‐mediated [4+4] photocyclodimerization of anthracene, which can be reversibly transformed by photoreversible dynamic covalent bonds. The polymers show decent phosphorescence emission with different colors at room temperature, achieving the conversion between blue phosphorescence and cyan phosphorescence. This study provides a novel method for designing and synthesizing pure organic RTP materials with tunable emissions through dynamic covalent bonds.

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Reaktivität in Molekularen Gefäßen: Beschleunigungsmodi und Arten der Erzielbaren Selektivität

Syntrivanis,

Tiefenbacher

2024

Angewandte Chemie

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There is increasing interest in the discovery and application of molecular flasks ‐ supramolecular host structures capable of catalyzing organic reactions. Reminiscent of enzymes due to possessing a host cavity akin to an active site, molecular flasks can exhibit complex catalytic mechanisms and in many cases provide selectivity not achievable in bulk solvent. In this Review, we aim to organize the increasingly diverse examples through a two‐part structure. In part one, we provide an overview of the different acceleration modes that operate within molecular flasks, while in part two we showcase, through selected examples, the different types of selectivity that are obtainable through the use of molecular flasks. Particular attention is given to examples that are relevant to current challenges in synthetic organic chemistry. We believe that this structure makes the field more approachable and thus will stimulate the development of novel applications of molecular flasks.

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Catalysis in Cyclodextrin-Based Unconventional Reaction Media: Recent Developments and Future Opportunities

Abstract: International audienceno abstrac

Cited by 56 publications

References 68 publications

Cucurbiturils as Reaction Containers for Photocycloaddition of Olefins

Cucurbiturils as Reaction Containers for Photocycloaddition of Olefins

Emission‐Tunable Room‐Temperature Phosphorescent Polymers Based on Dynamic Reversible Supramolecule‐Mediated Photocrosslinking

Reaktivität in Molekularen Gefäßen: Beschleunigungsmodi und Arten der Erzielbaren Selektivität

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