Transforming Porous Organic Cages into Porous Ionic Liquids via a Supramolecular Complexation Strategy

Jie, Kecheng; Onishi, Nicole; Schott, Jennifer A.; Popovs, Ilja; Jiang, De‐en; Mahurin, Shannon M.; Dai, Sheng

doi:10.1002/ange.201912068

Cited by 31 publications

(17 citation statements)

References 26 publications

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“…93 An alternative recent approach for higher PLs having higher CO 2 adsorption capacity included type I ionic liquid PL. 94 This PL was formed by reacting crown ethers and a potassium carboxylate group appended diamine (KCDA), see Figure 6C. KDCA is a ligand for the synthesis of an imine-based anionic covalent cage (ACC).…”

Section: Emerging Applications Separationsmentioning

confidence: 99%

“…The CO 2 uptake reached 0.429 mmol/g, resulting from the large cage diameters and high cage loading in the final PL compounds. 94 Interestingly, when combining the adsorptive properties of RTILs with porous cages to design an ionic liquid PL with the Zn 4 L 4 cation cage, the size and molecular shape selectivity of the new type I PLs were dictated by the pore entrance width and shape dictated by the Zn 4 L 4 tetrahedra. The cage dimensions were the defining element for the adsorption and interaction strength of chlorofluorocarbons.…”

Section: Emerging Applications Separationsmentioning

confidence: 99%

“…(C) Reaction scheme between a crown ether and a potassium carboxylate group appended diamine (KCDA) yielding novel type I PL where the cation is positively charged crown ether-potassium complex. Reprinted with permission from Jie et al94 ª 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. (D) CO 2 adsorption-desorption isotherms of HCS-liquid, PEGS, SCS-liquid (SCS, solid carbon spheres), and PILs-PEGS composite collected below 10 bar at 298 K, respectively.…”

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confidence: 99%

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Porous Liquids: The Next Frontier

Fulvio

Dai

2020

Chem

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Section: Emerging Applications Separationsmentioning

confidence: 99%

Section: Emerging Applications Separationsmentioning

confidence: 99%

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Porous Liquids: The Next Frontier

Fulvio

Dai

2020

Chem

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“…Type 1 PLs consist of a neat liquid that is composed of molecules with stable intrinsic porosity, for example a liquid formed of hollow nanospheres . Type 2 PLs consist of a rigid porous host and a solvent that is sterically hindered from entering the pore cavity, for example, a porous organic cage molecule solvated in large crown-ether molecules . Type 3 PLs consist of a solvated nanoporous particle, rather than distinct porous cages, in a sterically hindered solvent.…”

Section: Overview Of Porous Liquids (Pls)mentioning

confidence: 99%

Porous Liquids: Computational Design for Targeted Gas Adsorption

Rimsza

Nenoff

2022

ACS Appl. Mater. Interfaces

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In this Perspective, we present the unique gas adsorption capabilities of porous liquids (PLs) and the value of complex computational methods in the design of PL compositions. Traditionally, liquids only contain transient pore space between molecules that limit long-term gas capture. However, PLs are stable fluids that that contain permanent porosity due to the combination of a rigid porous host structure and a solvent. PLs exhibit remarkable adsorption and separation properties, including increased solubility and selectivity. The unique gas adsorption properties of PLs are based on their structure, which exhibits multiple gas binding sites in the pore and on the cage surface, varying binding mechanisms including hydrogen-bonding and π–π interactions, and selective diffusion in the solvent. Tunable PL compositions will require fundamental investigations of competitive gas binding mechanisms, thermal effects on binding site stability, and the role of nanoconfinement on gas and solvent diffusion that can be accelerated through molecular modeling. With these new insights PLs promise to be an exceptional material class with tunable properties for targeted gas adsorption.

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“…The functionalization of their periphery with alkyl chains 24,25 or poly(ethylene glycol) chains 4 offers opportunities to reduce the melting point, giving rise to the Type I porous liquids. Another synthetic approach of Type I porous liquids is to transform the anionic POC into ionic liquid by pairing with cationic 18-crown-6/K + complex 26 . However, most of molecular cage-derived porous liquids are generated via dissolving molecular cages in bulky solvents, also known as Type II porous liquids.…”

Section: Introductionmentioning

confidence: 99%

Type II porous ionic liquid based on metal-organic cage that enables L-tryptophan identification

Zhang

Yang

Zhang

et al. 2021

Preprint

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Porous liquids with chemical separation properties are quite well-studied in general, but there is only a handful of reports in the context of identification and separation of non-gaseous molecules. Herein, we report the first example of Type-II porous ionic liquid that exhibits exceptional selectivity towards L-tryptophan (L-Trp) over other aromatic amino acids and the first in which coordination cages promote this selectivity. A previously known class of anionic organic-inorganic hybrid doughnut-like cage (HD) has been readily dissolved in trihexyltetradecylphosphonium chloride (THTP_Cl). The resulting liquid, HD/THTP_Cl, is thereby composed of common components, facile to prepare, and exhibit room temperature fluidity. The permanent porosity are manifested by the high-pressure isotherm for CH4 and modeling studies. With evidence from time-dependent amino acid uptake, competitive extraction studies and molecular dynamic simulations, HD/THTP_Cl exhibit better selectivity towards L-Trp than existing solid state sorbents, and we attribute it to not only the intrinsic porosity of HD but also the host-guest interactions between HD and L-Trp. Specifically, each HD unit is binded with nearly 5 L-Trp molecules, which is higher than the L-Trp occupation in the structure unit of other benchmark metal-organic frameworks.

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Transforming Porous Organic Cages into Porous Ionic Liquids via a Supramolecular Complexation Strategy

Abstract: This is the author manuscript accepted for publication and has undergone full peer review but has not been through the copyediting, typesetting, pagination and proofreading process, which may lead to differences between this version and the Version of Record.

Cited by 31 publications

References 26 publications

Porous Liquids: The Next Frontier

Porous Liquids: The Next Frontier

Porous Liquids: Computational Design for Targeted Gas Adsorption

Type II porous ionic liquid based on metal-organic cage that enables L-tryptophan identification

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