Cucurbitimines – imine cages with concave walls

Bourguignon, Christine; Schindler, Dorothee; Zhou, G. X.; Röminger, Frank; Mastalerz, Michael

doi:10.1039/d1qo00478f

Cited by 5 publications

(6 citation statements)

References 91 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…(i) DCM, 2 mol % TFA, rt, 7 days. Comparison of the molecular pore volumes of ( R , R ) cucurbitimines [3 + 6] and [4 + 8] with cucurbiturils CB6 and CB8 . Adapted with permission from ref .…”

Section: Cages and Containers Soluble In Organic Solvents And Their A...mentioning

confidence: 99%

“…Comparison of the molecular pore volumes of ( R , R ) cucurbitimines [3 + 6] and [4 + 8] with cucurbiturils CB6 and CB8 . Adapted with permission from ref . Copyright 2021 the authors of the original publication.…”

Section: Cages and Containers Soluble In Organic Solvents And Their A...mentioning

confidence: 99%

“…147 Mastalerz and co-workers applied a Guest exchange was also studied, and the authors found that THF was exchanged by toluene on more than 2 days at room temperature or in less than 1 h at 100 °C (Figure 58). 148 Zhang, Liu X., Liu Z., and co-workers employed precursors 47b and 195 to prepare catenanes 196 and 197. Catenane 198 is formed by two dissymmetric cages by means of a spacediscriminative postassembly modification strategy using a voluminous reductant like NaBH(OAc) 3 to selectively reduce the outer imine bonds.…”

Section: Capsules and Cagesmentioning

confidence: 99%

See 2 more Smart Citations

Purely Covalent Molecular Cages and Containers for Guest Encapsulation

et al. 2022

View full text Add to dashboard Cite

Cage compounds offer unique binding pockets similar to enzyme-binding sites, which can be customized in terms of size, shape, and functional groups to point toward the cavity and many other parameters. Different synthetic strategies have been developed to create a toolkit of methods that allow preparing tailor-made organic cages for a number of distinct applications, such as gas separation, molecular recognition, molecular encapsulation, hosts for catalysis, etc. These examples show the versatility and high selectivity that can be achieved using cages, which is impossible by employing other molecular systems. This review explores the progress made in the field of fully organic molecular cages and containers by focusing on the properties of the cavity and their application to encapsulate guests.

show abstract

Section: Cages and Containers Soluble In Organic Solvents And Their A...mentioning

confidence: 99%

Section: Cages and Containers Soluble In Organic Solvents And Their A...mentioning

confidence: 99%

Section: Capsules and Cagesmentioning

confidence: 99%

See 1 more Smart Citation

Purely Covalent Molecular Cages and Containers for Guest Encapsulation

et al. 2022

View full text Add to dashboard Cite

show abstract

“…Covalent organic cages are a class of discrete porous architectures with accessible cavities made from organic monomers linked by covalent interactions and have been extensively studied for many potential applications. − However, with the exception of few cases involving mixed linkers, − no organic cages have been reported to have the same composition but different topology structures. Here, we illustrated the structural isomerism of chiral [4 + 8] organic cages with totally different topologies and geometries that display isomer-dependent enantioselective catalytic activities.…”

Section: Introductionmentioning

confidence: 99%

Chiral Covalent Organic Cages: Structural Isomerism and Enantioselective Catalysis

Wang,

Tang,

Anjali

et al. 2024

J. Am. Chem. Soc.

View full text Add to dashboard Cite

Covalent organic cages are a prominent class of discrete porous architectures; however, their structural isomerism remains relatively unexplored. Here, we demonstrate the structural isomerism of chiral covalent organic cages that renders distinct enantioselective catalytic properties. Imine condensations of tetratopic 5,10-di(3,5-diformylphenyl)-5,10-dihydrophenazine and ditopic 1,2-cyclohexanediamine produce two chiral [4 + 8] organic cage isomers with totally different topologies and geometries that depend on the orientations of four tetraaldehyde units with respect to each other. One isomer (PN-1) has an unprecedented Johnsontype J 26 structure, whereas another (PN-2) adopts a tetragonal prismatic structure. After the reduction of the imine linkages, the cages are transformed into two amine bond-linked isomers PN-1R and PN-2R. After binding to Ni(II) ions, both can serve as efficient catalysts for asymmetric Michael additions, whereas PN-2R affords obviously higher enantioselectivity and reactivity than PN-1R presumably because of its large cavity and open windows that can concentrate reactants for the reactions. Density-functional theory (DFT) calculations further confirm that the enantioselective catalytic performance varies depending on the isomer.

show abstract

“…9,26 Most cage compounds are synthesized by dynamic covalent chemistry (DCC). 27 Among DCC reactions, the reactions forming boronic acid esters or imines are the most common ones and for the latter a huge variety of geometries such as (truncated) 28,29 tetrahedra, [30][31][32][33] trigonal prisms, [34][35][36] cubes, 16,37,38 rhombicuboctahedra, [39][40][41] adamantoids, 35,42,43 tetrapods, 44 cucurbitimines 45 or more complex structures such as catenanes 46,47 have been realized and some of these structures have even been post-stabilized to enhance their chemical robustness. 6,[48][49][50] Cages with nitrogen-containing pyridine 9,51 or pyrrol-units 52 showed superior behavior in, e.g., ion recognition and could act as ligands for several transition metal ions as shown for numerous metal-organic cage compounds or complexes.…”

Section: Introductionmentioning

confidence: 99%