Oriented Two‐Dimensional Porous Organic Cage Crystals

Jiang, Shan; Song, Qilei; Massey, Andrew; Chong, Samantha Y.; Chen, Linjiang; Sun, Shijing; Hasell, Tom; Raval, Rasmita; Sivaniah, Easan; Cheetham, Anthony K.; Cooper, Andrew I.

doi:10.1002/anie.201704579

Cited by 33 publications

(29 citation statements)

References 45 publications

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“…[247] Oriented thin films on various substrates were obtained by solution processing. [248,249] In addition, cages were implemented in hybrid composite membranes together with porous organic polymers [250] or as additives in macroscopic inorganic porous beads. [251] Fort ernary mixtures,p orous organic alloys could be produced with one cage occupying 50 %o ft he lattice positions and the other two components being statistically distributed across the other sites in any ratio to form as olid solution.…”

Section: Processability and Morphology Controlmentioning

confidence: 99%

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

2018

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Porous organic materials are an emerging class of functional nanostructures with unprecedented properties. Dynamic covalent assembly of small organic building blocks under thermodynamic control is utilized for the intriguingly simple formation of complex molecular architectures in one-pot procedures. In this Review, we aim to analyze the basic design principles that govern the formation of either covalent organic frameworks as crystalline porous polymers or covalent organic cage compounds as shape-persistent molecular objects. Common synthetic procedures and characterization techniques will be discussed as well as more advanced strategies such as postsynthetic modification or self-sorting. When appropriate, comparisons are drawn between polymeric frameworks and discrete organic cages in terms of their underlying properties. Furthermore, we highlight the potential of these materials for applications ranging from gas storage to catalysis and organic electronics.

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Section: Processability and Morphology Controlmentioning

confidence: 99%

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

2018

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“…Molecular crystals are usually maintained by stronger intermolecular interactions such as hydrogen bonds or electrostatic forces. [8][9][10][14][15][16][17][18][19][20][21][22][23][34][35][36][37][38] The methanol content in DNT-MeOH ( Figure S6, Supporting Information) was estimated from the number of diffuse electrons determined by the SQUEEZE routine [39] within the solvent accessible voids, after eliminating the contribution of the bromide anions (96 × 36 e). The determined electrons correspond to approx.…”

Section: A Chiral Bis-naphthylated Tetrandrine Dibromide: Synthesis mentioning

confidence: 99%

A Chiral Bis‐Naphthylated Tetrandrine Dibromide: Synthesis, Self‐Assembly into an Organic Framework Based On Nanosized Spherical Cages, and Inclusion Studies

et al. 2019

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Crystalline framework materials have gained interest because of their many potential applications. A novel chiral tetrandrine salt (DNT) has been synthesized and characterized by conventional analytical techniques and single‐crystal X‐ray diffraction analysis, and its self‐assembly behavior studied. In the solid state, 48 molecules of the compound self‐assemble into an organic framework based on nanospherical aggregates formed exclusively through weak noncovalent interactions. Additionally, it was demonstrated by UV‐vis spectroscopy and TGA that assembled DNT can include the Nile Red dye, giving a fluorescent material. To the best of our knowledge, these spherical assemblies are the largest among the purely synthetic organic self‐assembled molecular crystals reported to date.

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“…Recently, the challenge of depositing crystalline films was successfully overcome by Cooper and co‐workers who grew oriented cage crystals on silicon wafers and glass substrates . Starting again from solutions of CC3 in dichloromethane or chloroform, but using the simple technique of dip coating, multiple 1.41 nm thick oriented cage layers could be deposited, resulting in hexagonal‐shaped 2D crystals with an average thickness of 200 nm and a diameter between 3 and 5 µm (Figure F).…”

Section: Porous Organic Molecular Materials Thin Filmsmentioning

confidence: 99%

Bringing Porous Organic and Carbon‐Based Materials toward Thin‐Film Applications

Wuttke

Medina

Rotter

et al. 2018

Adv Funct Materials

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Porous materials have attracted tremendous scientific and industrial interest due to their broad commercial applicability. However, some applications require that these materials are deposited on surfaces to create thin films. Here, the recent progress of new porous thin-film material classes is described: porous organic molecular materials, porous organic polymers, covalent organic frameworks, and nanoporous carbon. In each case, the state of the art and current barriers in their thin-film fabrication, as well as intrinsic material advantages that are suited for different applications are presented. By highlighting the unique structural characteristics and properties of these materials, it is hoped that increased research development and industrial interest will be fostered, which will lead to new methods of thin-film synthesis and consequently to new applications. Figure 2. 1) Structure, crystal packing and BET surface area of triptycene trisbenzimidazolone (TTBI), 2) structure and BET surface area of OMIM-10-14, 3) structure of Doonan cage C1 and BET surface area of the two different crystalline polymorphs obtained by slow and fast precipitation, 4) structure and BET surface area of a triptycene-based cage, 5) structure of Cooper Cage CC3 (cyclohexyl vertices). A) Schematic low-energy crystal packings for CC1 (hydrogens on vertices; formally nonporous), CC2 (methyl vertices; 1D external pore channels), and CC13 (dimethyl vertices; 2D layered pore structure with formally disconnected voids). As such, small structural changes to the vertex groups lead to three quite different crystal packings and pore topologies for the α polymorphs shown here (orange = disconnected voids; yellow = interconnected pores). Crystallization in the presence of 1,4-dioxane causes pseudoisostructural window-to-window packing for all three cage modules, causing the materials to mimic the 3D diamondoid pore structure of CC3 shown in D. B) N 2 sorption isotherms (77 K) for homochiral CC3 produced by freeze-drying (green diamonds, 6 repetitions), vacuum evaporation (blue triangles), standard reaction (black squares), and slow crystallization (red circles, 6 repetitions). C,D) Molecular simulation of amorphous packing (top) and crystalline structure (bottom) of CC3, with the Connolly surface probed by N 2 molecules (kinetic diameter of 3.64 Å) shown in blue, and average BET surface area extracted from the isotherms shown in (B). 1) Reproduced with permission. [58] Figure 12. A) CDC thin-film synthesis and EDLC test cell preparation. Titanium is extracted from titanium carbide as TiCl 4 , forming a porous carbon film. Two carbide plates with the same CDC coating thickness are placed face to face and separated by a polymer fabric soaked with electrolyte. The SEM image (left) shows a representative image of a CDC/TiC interface with a good film adhesion. Reproduced with permission. [187]

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Oriented Two‐Dimensional Porous Organic Cage Crystals

Cited by 33 publications

References 45 publications

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

Covalent Organic Frameworks and Cage Compounds: Design and Applications of Polymeric and Discrete Organic Scaffolds

A Chiral Bis‐Naphthylated Tetrandrine Dibromide: Synthesis, Self‐Assembly into an Organic Framework Based On Nanosized Spherical Cages, and Inclusion Studies

Bringing Porous Organic and Carbon‐Based Materials toward Thin‐Film Applications

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