Creating porosity in a trianglimine macrocycle by heterochiral pairing

He, Donglin; Clowes, Rob; Little, Marc A.; Liu, Ming; Cooper, Andrew I.

doi:10.1039/d1cc01650d

Cited by 14 publications

(20 citation statements)

References 42 publications

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“…Isotrianglimines, although not easy “in collaboration” as calixsalens, are characterized by their not fully explored potential in crystal engineering. The propensity of these compounds to form hybrid materials consisting of molecules differing in their absolute configuration (the heterochiral pairing strategy proposed Cooper) 56 or substitution pattern (formation of cocrystals or solid solutions) is especially interesting. Although the results presented here do not confirm the last hypothesis, the work on this current topic is in progress.…”

Section: Discussionmentioning

confidence: 99%

“…Only recently has Cooper et al reported crystal structures of optically pure and racemic 3a . 56 In the crystal, the optically pure 3a molecules form pillars containing solvent molecules in their cavities. A heterochiral pairing strategy introduced porosity when ( rac )- 3a was crystallized and packed in the lattice using head-to-head supramolecular motifs.…”

Section: Introductionmentioning

confidence: 99%

“…As a result, a porous material was obtained that was characterized by the highest reported SA BET of 355 m 2 g –1 for trianglimine-like macrocycle and exhibited a high selectivity toward the separation of para -xylene from the mixture of isomers. 56 …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Specific Noncovalent Association of Truncated exo-Functionalized Triangular Homochiral Isotrianglimines through Head-to-Head, Tail-to-Tail, and Honeycomb Supramolecular Motifs

et al. 2022

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Chiral isotrianglimines were synthesized by the [3 + 3] cyclocondensation of ( R , R )-1,2-diaminocyclohexane with C5-substituted isophthalaldehyde derivatives. The substituent’s steric and electronic demands and the guest molecules’ nature have affected the conformation of individual macrocycles and their propensity to form supramolecular architectures. In the crystal, the formation of a honeycomb-like packing arrangement of the simplest isotrianglimine was promoted by the presence of toluene or para -xylene molecules. A less symmetrical solvent molecule might force this arrangement to change. Polar substituents present in the macrocycle skeleton have enforced the self-association of isotrianglimines in the form of tail-to-tail dimers. These dimers could be further arranged in higher-order structures of the head-to-head type, which were held together by the solvent molecules. Non-associating isotrianglimine formed a container that accommodated acetonitrile molecules in its cavity. The calculated dimerization energies have indicated a strong preference for the formation of tail-to-tail dimers over those of the capsule type.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Specific Noncovalent Association of Truncated exo-Functionalized Triangular Homochiral Isotrianglimines through Head-to-Head, Tail-to-Tail, and Honeycomb Supramolecular Motifs

et al. 2022

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“…Crystallization of chiral tiranglimine macrocycle using a heterochiral paring strategy may introduce porosity into the crystal framework. This was observed in the macrocyclic polyiminines that do not exhibit high porosity in the enantiopure form [ 64 ]. Cooper at al proved this using the example of a simple triangilimine derived from condensation of trans -1,2-diaminocyclohexane and isophthalic aldehyde.…”

Section: Nitrogen-containing Macrocycles—applicationsmentioning

confidence: 98%

Recent Advances in the Synthesis and Applications of Nitrogen-Containing Macrocycles

Grajewski

2022

Molecules

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Macrocyclic nitrogen-containing compounds are versatile molecules. Supramolecular, noncovalent interactions of these macrocycles with guest molecules enables them to act as catalysts, fluorescent sensors, chiral or nonchiral selectors, or receptors of small molecules. In the solid state, they often display a propensity to form inclusion compounds. All of these properties are usually closely connected with the presence of nitrogen atoms in the macrocyclic ring. As most of the reviews published so far on macrocycles were written from the viewpoint of functional groups, synthetic methods, or the structure, search methods for literature reports in terms of the physicochemical properties of these compounds may be unobvious. In this minireview, the emphasis was put on the synthesis and applications of nitrogen-containing macrocyclic compounds, as they differ from their acyclic analogs, and at the same time are the driving force for further research.

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“…Hence, Cooper et al . recently revisited the iso ‐TA based macrocycle T1 regarding the porosity of the system, speculating that the adsorption kinetics can be enhanced [26b] . Gas adsorption experiments with R ‐ T1 showed that activation of the crystalline sample resulted in a basically non‐porous polycrystalline material ( SA BET ≈4 m 2 g −1 ), due to collapsing of the pores upon solvent removal.…”

Section: Triangliminesmentioning

confidence: 99%

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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Creating porosity in a trianglimine macrocycle by heterochiral pairing

Abstract: Macrocycles are usually non-porous or barely porous in the solid-state because of their small intrinsic cavity sizes and tendency to close-pack. Here, we use a heterochiral pairing strategy to introduce...

Cited by 14 publications

References 42 publications

Specific Noncovalent Association of Truncated exo-Functionalized Triangular Homochiral Isotrianglimines through Head-to-Head, Tail-to-Tail, and Honeycomb Supramolecular Motifs

Specific Noncovalent Association of Truncated exo-Functionalized Triangular Homochiral Isotrianglimines through Head-to-Head, Tail-to-Tail, and Honeycomb Supramolecular Motifs

Recent Advances in the Synthesis and Applications of Nitrogen-Containing Macrocycles

Porous Organic Compounds – Small Pores on the Rise

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