Rational Design of Multifunctional Nanopores by Mixing Matching Molecules

Mastalerz, Michael

doi:10.1002/anie.201107828

Cited by 17 publications

(17 citation statements)

References 38 publications

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“…The preparations of 9 , 10 , 12 , 14 – 19 , 23 , 26 , and 29 have been reported previously. 18 , 19 , 22 Procedures for the remaining compounds in Charts 2 and 3 are given in the Supporting Information .…”

Section: Resultsmentioning

confidence: 99%

“…For example, starting at nearly 20% (for 2 ), the volume available in the pores can be tuned downward in small increments essentially to zero (for 15 and 19 ). Indeed, by taking advantage of alloy formation, 19 continuous variation should be possible with these compounds. Unsurprisingly, pore volumes and diameters are generally determined by the size of the terminal groups, but more subtle effects are also in play.…”

Section: Resultsmentioning

confidence: 99%

“…We have described a series of three NPSUs with aromatic groups in R 2 , and the interesting feature of “water wires” in the channels, 18 and also a range of NPSU-based organic alloys. 19 Herein we provide a more complete description of our work surveying the scope and properties of NPSUs, drawing on 25 examples which have been characterized by X-ray crystallography. We show how the dimensions and shapes of the channels can be tuned, and how their chemical nature can be altered by the introduction of functional groups (including previously unreported alkene and aldehyde functionality).…”

Section: Introductionmentioning

confidence: 99%

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Tunable Porous Organic Crystals: Structural Scope and Adsorption Properties of Nanoporous Steroidal Ureas

et al. 2013

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Previous work has shown that certain steroidal bis-(N-phenyl)ureas, derived from cholic acid, form crystals in the P61 space group with unusually wide unidimensional pores. A key feature of the nanoporous steroidal urea (NPSU) structure is that groups at either end of the steroid are directed into the channels and may in principle be altered without disturbing the crystal packing. Herein we report an expanded study of this system, which increases the structural variety of NPSUs and also examines their inclusion properties. Nineteen new NPSU crystal structures are described, to add to the six which were previously reported. The materials show wide variations in channel size, shape, and chemical nature. Minimum pore diameters vary from ∼0 up to 13.1 Å, while some of the interior surfaces are markedly corrugated. Several variants possess functional groups positioned in the channels with potential to interact with guest molecules. Inclusion studies were performed using a relatively accessible tris-(N-phenyl)urea. Solvent removal was possible without crystal degradation, and gas adsorption could be demonstrated. Organic molecules ranging from simple aromatics (e.g., aniline and chlorobenzene) to the much larger squalene (Mw = 411) could be adsorbed from the liquid state, while several dyes were taken up from solutions in ether. Some dyes gave dichroic complexes, implying alignment of the chromophores in the NPSU channels. Notably, these complexes were formed by direct adsorption rather than cocrystallization, emphasizing the unusually robust nature of these organic molecular hosts.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Tunable Porous Organic Crystals: Structural Scope and Adsorption Properties of Nanoporous Steroidal Ureas

et al. 2013

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“…It is envisioned that crystalline assemblies prepared from appropriate combinations of organic and/or metal-organic building blocks will afford functional materials that exhibit targeted bulk properties. Desirable bulk properties include inter alia porosity, catalysis, magnetism, conductivity, luminescence, and non-linear optical activity [1][2][3][4][5][6][7][8][9][10][11][12]. Of these targeted functions, the construction of porous crystalline materials has garnered considerable attention, in large part spurred by the desire to identify energy-related materials that can be potentially used for reversible gas storage [13][14][15].…”

Section: Introductionmentioning

confidence: 99%

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Gabr

Pigge

2018

Crystals

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Tetraarylethylene derivatives are emerging as an increasingly important family of supramolecular building blocks in both solution phase and the solid state. The utility of tetraarylethylenes stems from appealing structural features (rigidity and symmetry) and their propensity to exhibit aggregation induced emission (AIE). In an effort to investigate the luminescent sensing ability of heteroaromatic tetraarylethylenes, we previously prepared tetra(4-pyridyl)ethylene and characterized its solution phase AIE properties. We here report the successful incorporation of tetra(4-pyridyl)ethylene into three distinct salts and co-crystalline assemblies with three organic di-carboxylic acids (oxalic acid, malonic acid, and fumaric acid). Interactions between the tetra(pyridyl)ethylene and di-acid components were found to vary from conventional to charge-assisted hydrogen bonding according to the extent of proton transfer between the acid and pyridine groups. Notably, the formation of pyridinium-carboxylate adducts in the salts does not appear to be strongly correlated with acid pKa. Three distinct network topologies were observed, and all featured the bridging of two or three tetra(pyridyl)ethylene groups through di-acid linkers. Crystalline assemblies also retained the AIE activity of tetra(pyridyl)ethylene and were luminescent under UV light. As tetra(4-pyridyl)ethylene features four Lewis basic and potentially metal ligating pyridine rings in a relatively well-defined geometry, this compound represents an attractive building block for the design of additional crystalline organic and metal-organic functional materials.

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“…[34] Cage compounds with the same exterior but different functional groups in their cavities can lead to a completely new type of porous materials with "pore-function on demand" by simple mixing of various cage compounds with different cavities to get amorphous materials or, more sophisticated, by co-crystallisation to get multifunctional porous materials (Scheme 4). Fundamental studies on co-crystallizing pore functionalities [50] or different cage compounds [22] give a first idea of what will be possible in the next decades to create multifunctional porous materials by using compatible discrete organic molecules.…”

Section: Discussionmentioning

confidence: 99%

Permanent Porous Materials from Discrete Organic Molecules—Towards Ultra‐High Surface Areas

Mastalerz

2012

Chemistry A European J

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215

140

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In recent years, the development of porous materials derived from discrete organic molecules made a substantial progress towards high-surface-area materials with distinct properties. One major advantage in comparison to existing, well-established porous polymers is their solubility, making such compounds potential valuable precursors for "processing porosity". One important parameter of porous compounds is their specific surface area. The possibilities to reach ultra-highsurface-area materials from this new type of porous compounds are critically discussed.

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Rational Design of Multifunctional Nanopores by Mixing Matching Molecules

Cited by 17 publications

References 38 publications

Tunable Porous Organic Crystals: Structural Scope and Adsorption Properties of Nanoporous Steroidal Ureas

Tunable Porous Organic Crystals: Structural Scope and Adsorption Properties of Nanoporous Steroidal Ureas

Salts and Co-Crystalline Assemblies of Tetra(4-Pyridyl)Ethylene with Di-Carboxylic Acids

Permanent Porous Materials from Discrete Organic Molecules—Towards Ultra‐High Surface Areas

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