A porous fluorinated organic [4+4] imine cage showing CO<sub>2</sub>and H<sub>2</sub>adsorption

Kunde, Tom; Nieland, Esther; Schröder, Hendrik V.; Schalley, Christoph A.; Schmidt, Bernd

doi:10.1039/d0cc01872d

Cited by 54 publications

(51 citation statements)

References 49 publications

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“…Only few articles focus on the role of fluorine in dynamic imine chemistry and as the possibility to influence porosity and guest‐binding behavior of POCs [10b,11] . Recently, we were able to demonstrate the beneficial effect of fluorine substitution [12] towards gas adsorption of POCs [13] …”

Section: Figurementioning

confidence: 99%

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages

Kunde

Pausch

Schmidt

2021

Chemistry A European J

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To create innovative materials, efficient control and engineering of pore sizes and their characteristics, crystallinity and stability is required. Eight hybrid Tri4Di6 imine cages with a tunable degree of fluorination and one fully fluorinated Tri4Di6 imine cage are investigated. Although the fluorinated and the non‐fluorinated building blocks used herein differ vastly in reactivity, it was possible to gain control over the outcome of the self‐assembly process, by carefully controlling the feed ratio. This represents the first hybrid material based on fluorinated/hydrogenated porous organic cages (POCs). These cages with unlimited miscibility in the solid state were obtained as highly crystalline samples after recrystallization and even showed retention of the crystal lattice, forming alloys. All mixtures and the fully fluorinated Tri4Di6 imine cage were analyzed by MALDI‐MS, single‐crystal XRD, powder XRD and in regard to thermal stability (TGA).

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Section: Figurementioning

confidence: 99%

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages

Kunde

Pausch

Schmidt

2021

Chemistry A European J

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“…Very recently Schmidt et al utilized trifluro substituted counterpart ( 9d ) of 9 to afford [4+4] imine cage 13 with trisformylbenzene 10a (Scheme 6). [ 16 ] MM2 calculation revealed the rotational energy barrier around sp 3 C– sp 2 C bond of 9d was much lower than 9b and undoubtedly it was not supposed to be properly oriented to lead desired cage formation but still the reaction provided moderate yield of the crystalline cage. The authors envisioned electronic effect of fluorine might have been played vital role to provoke the generation of cage motif unlike the steric crowding effect of alkyl groups in other substrates.…”

Section: Aliphatic Triamine Based Oics: Syntheses Special Featurementioning

confidence: 99%

Recent Advances in Tris‐Primary Amine Based Organic Imine Cages and Related Amine Macrocycles

2020

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Molecules bearing three primary amine groups are ubiquitous substances in various fields of synthetic chemistry. Some of them are commercially available and the rests are emerged from the designed protocols of synthetic chemists. It has been observed that such aliphatic as well as aromatic triamines are excellent precursors for the design and synthesis of various cage molecules of which organic imine cages (OICs) and related amine macrocycles belong to the category of special interest. These compounds possess unique architectures and already made their marks in the field of supramolecular chemistry, synthetic methodology, and material science. In this review we aimed to consider recent reports that highlighted the syntheses, special features, and applications of primary triamine based OICs and related amine macrocycles.

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“…Nowadays, shape‐persistent organic cages are mainly synthesized by using reversible condensation reactions, such as by multiple imine bond formation or the generation of boronic esters from the corresponding diols and boronic acids [20–60] . These reactions used are often called dynamic covalent chemistry (DCC) reactions, allowing the system to reach thermodynamic equilibrium by self‐correction mechanisms due to the intrinsic reversibility [5,61,62] .…”

Section: Introductionmentioning

confidence: 99%

Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages

Holsten

Feierabend

Elbert

et al. 2021

Chemistry A European J

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One of the most applied reaction types to synthesize shape-persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine condensation. However, most of the synthesized imine cages reported are formed as precipitate from the reaction mixture and therefore rather may be kinetically controlled products. There are even examples in literature, where resulting cages are not soluble at all in common organic solvents to characterize or study their formation by NMR spectroscopy in solution. Here, a triptycene triamine containing three solubilizing n-hexyloxy chains has been used to synthesize soluble congeners of prior insoluble cages. This allowed us to study the formation as well as the reversibility of cage formation in solution by investigating exchange of building blocks between the cages and deuterated derivatives thereof.

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A porous fluorinated organic [4+4] imine cage showing CO₂and H₂adsorption

Abstract: We report the first POC, containing perfluorinated aromatic panels forming quickly and in high purity, despite low preorganization encoded in the starting materials.

Cited by 54 publications

References 49 publications

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages

Recent Advances in Tris‐Primary Amine Based Organic Imine Cages and Related Amine Macrocycles

Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages

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A porous fluorinated organic [4+4] imine cage showing CO2and H2adsorption

Abstract: We report the first POC, containing perfluorinated aromatic panels forming quickly and in high purity, despite low preorganization encoded in the starting materials.

Cited by 54 publications

References 49 publications

Supramolecular Alloys from Fluorinated Hybrid Tri4Di6Imine Cages

Supramolecular Alloys from Fluorinated Hybrid Tri4Di6Imine Cages

Recent Advances in Tris‐Primary Amine Based Organic Imine Cages and Related Amine Macrocycles

Soluble Congeners of Prior Insoluble Shape‐Persistent Imine Cages

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A porous fluorinated organic [4+4] imine cage showing CO₂and H₂adsorption

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages

Supramolecular Alloys from Fluorinated Hybrid Tri⁴Di⁶Imine Cages