Porous shape-persistent rylene imine cages with tunable optoelectronic properties and delayed fluorescence

Huang, Hsin-Hua; Song, Kyung Seob; Prescimone, Alessandro; Aster, Alexander; Cohen, Gabriel; Mannancherry, Rajesh; Vauthey, Eric; Coskun, Ali; Šolomek, Tomáš

doi:10.1039/d1sc00347j

Cited by 24 publications

(23 citation statements)

References 91 publications

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“…Cages RC1 and RC2 also both showed higher affinity towards CO 2 , with capacities of 2.0 and 2.9 mmol g −1 , respectively. Moreover, they even showed CO 2 /N 2 selectivity and CH 4 uptake [19b] . These results also suggest the benefits of precise pore control and electron‐deficient nanocavities, complementing ongoing POC research.…”

Section: Porous Organic Cagesmentioning

confidence: 56%

“…The synthesis of chiral Tri 2 Di 3 POCs incorporating rylene diimides and their molecular structures determined from SXRD. Hydrogen atoms and solvent molecules are omitted for clarity [19].…”

mentioning

confidence: 99%

“…Hydrogen atoms and solvent molecules are omitted for clarity, space-filling view including hydrogen atoms for showcasing the influence of adjacent groups on the window size. [19] porosity and a type I adsorption isotherm for (SA BET = 522 m 2 g À 1 ) upon activation by dynamic vacuum or with supercritical CO 2 . The small difference in building block size led to cage RC2 being shape-persistent, whereas RC1 showed a gate opening phenomenon, usually observed for soft porous crystals and flexible porous cages, where fast uptake of N 2 only occurred after a threshold pressure was reached.…”

mentioning

confidence: 99%

“…[18] A series of three rylene-type cages were investigated by the group of Šolomek, also extending the repertoire of POCs towards photochemistry (Figure 7). [19] The incorporated rylene diimides are not only interesting because of their strong adsorption and emission but they are also potent electron acceptors with favorable redox potentials.…”

mentioning

confidence: 99%

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Porous Organic Compounds – Small Pores on the Rise

2021

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Porous materials are important for various energy‐related technologies such as catalysis and separation. While porous organic cage compounds are a rather recent addition to the field of porous materials, these discrete nanocavities have since emerged as a versatile functional‐materials platform, facilitated by the solubility of the materials in common organic solvents. In contrast to other frameworks, organic cages are assembled first from modular building blocks in solution and then packed in the solid‐state in a next step. In this minireview, we highlight examples of porous organic cages with focus on how the intrinsic nanopore can be controlled and utilized, especially focusing on their synthesis and the gas sorption properties of smaller intrinsic pores of porous organic cage compounds, porous macrocycles, and other related compounds.

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Section: Porous Organic Cagesmentioning

confidence: 56%

mentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Porous Organic Compounds – Small Pores on the Rise

2021

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“…Porous organic cages (POCs) are newly emerging attractive crystalline molecular materials with great application potential in the fields of storage and separation, 1 sensing, 2 and catalysis. 3 Their advantages originate from the intrinsic and extrinsic voids together with the functional groups attached on POCs.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective assembly and recognition of heterochiral porous organic cages deduced from binary chiral components

Liu

Jin

et al. 2022

Chem. Sci.

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Fluorierte Squareimine zur molekularen Trennung von aromatischen und aliphatischen Verbindungen

Pausch,

Clopot,

Jordan

et al. 2024

Angewandte Chemie

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The development of more energy‐efficient separation technologies is essential. Especially the separation of cyclic aliphatic hydrocarbons from their aromatic counterparts remains a significant challenge due to azeotrope formation and similar physical properties, often requiring energy‐intensive processes. Herein, we introduce a novel class of electron‐deficient macrocycles with a unique rectangular structure to optimise π···π interactions within the pore, enabling the highly selective molecular sieving of aromatic compounds from mixtures. Utilising dynamic covalent imine chemistry, the squareimine NDI2F42‐based crystalline functional material is directly obtained from the reaction mixture in a single self‐assembly step in high yields of 84%, alongside the larger NDI2F82 congener, which can be obtained in 69% yield. In vapour sorption and diffusion experiments, NDI2F42 demonstrates rapid adsorption kinetics with selectivities of 97:3 for benzene over cyclohexane and 93:7 for toluene over methylcyclohexane, while single‐crystal and powder X‐ray diffraction studies confirm that the selectivity is primarily governed by directed π···π interactions.

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Porous shape-persistent rylene imine cages with tunable optoelectronic properties and delayed fluorescence

Abstract: Chiral rylene imine cages combine porosity and tunable optoelectronic properties. They adsorb CO2 over N2 with good selectivity and can show an efficient delayed fluorescence.

Cited by 24 publications

References 91 publications

Porous Organic Compounds – Small Pores on the Rise

Porous Organic Compounds – Small Pores on the Rise

Enantioselective assembly and recognition of heterochiral porous organic cages deduced from binary chiral components

Fluorierte Squareimine zur molekularen Trennung von aromatischen und aliphatischen Verbindungen

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