Nodal equivalence of (O–H)6 and aromatic rings: a supramolecular cousin of Dianin's compound and β-hydroquinone1,2

Nguyen, Vi T.; Bishop, Roger; Chan, Isa Y. H.; Craig, Donald C.; Scudder, Marcia L.

doi:10.1039/b809684h

Cited by 9 publications

(9 citation statements)

References 25 publications

(29 reference statements)

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“…However, it is impossible to simply sketch the structure of Dianin's compounds and determine how it would crystallize, without any prior structural knowledge, although one could infer, for example, that the hydroxy groups are likely to hydrogen bond. While the cyclic (OH) 6 hydrogen-bonded motif in the structure of Dianin's compound has been used to discover several structural analogues, [269][270][271][272][273] these cyclic (OH) 6 hydrogen-bonded motifs are rarely directional enough Figure 9. Synthesis of postsynthetically modified cage compounds reported by Mastalerz et al [258] Two different methods were used, with Method B developed to postsynthetically modify an endo-functionalized cage, using sixfold Williamson ether formation.…”

Section: Tuning Crystal Porosity By Controlling Molecular Packingmentioning

confidence: 99%

“…However, it is impossible to simply sketch the structure of Dianin's compounds and determine how it would crystallize, without any prior structural knowledge, although one could infer, for example, that the hydroxy groups are likely to hydrogen bond. While the cyclic (OH) 6 hydrogen‐bonded motif in the structure of Dianin's compound has been used to discover several structural analogues,269–273 these cyclic (OH) 6 hydrogen‐bonded motifs are rarely directional enough to dominate crystallization outcomes. Instead, several alternative design approaches have been developed for preserving the inefficient packing of molecules in porous solids.…”

Section: Tuning the Properties Of Porous Molecular Materialsmentioning

confidence: 99%

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The Chemistry of Porous Organic Molecular Materials

Little

Cooper

2020

Adv Funct Materials

257

189

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Porous organic molecular materials are a subclass of porous solids that are defined by their modular, molecular structures, and the absence of extended covalent or coordination bonding in the solid-state. As a result, porous molecular materials are soluble and they can be processed into different forms, such as mixed matrix membranes. The structure of the porous modules can be fine-tuned for specific applications, such as gas isotope separations, and in some cases the solid-state properties of these materials can be defined by the structure of the porous molecule as viewed in isolation. In this review, the authors focus on the design of porous organic molecular materials and how their properties can be tuned for specific applications by using crystal engineering techniques. The authors distinguish between strategies where porosity is defined largely by the molecule itself, for example, in porous organic cages, and cases where porosity is generated by the solidstate crystalline assembly. They emphasize the importance of computational techniques in the de novo design of functional, porous organic molecular materials, and how molecular modeling is applied to understand the properties of these materials.

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Section: Tuning Crystal Porosity By Controlling Molecular Packingmentioning

confidence: 99%

“…However, it is impossible to simply sketch the structure of Dianin's compounds and determine how it would crystallize, without any prior structural knowledge, although one could infer, for example, that the hydroxy groups are likely to hydrogen bond. While the cyclic (OH) 6 hydrogen‐bonded motif in the structure of Dianin's compound has been used to discover several structural analogues,269–273 these cyclic (OH) 6 hydrogen‐bonded motifs are rarely directional enough to dominate crystallization outcomes. Instead, several alternative design approaches have been developed for preserving the inefficient packing of molecules in porous solids.…”

Section: Tuning the Properties Of Porous Molecular Materialsmentioning

confidence: 99%

The Chemistry of Porous Organic Molecular Materials

Little

Cooper

2020

Adv Funct Materials

257

189

View full text Add to dashboard Cite

show abstract

“…37 Scheme 3 One cage in the Dianin's compound where each molecule is represented by a solid green rod (opposite enantiomers light or dark) with a solid sphere at each end (red, hydroxy group; orange, ether oxygen). 41 compound 42 is a well-known clathrand capable of hosting a variety of guests, typically in ratios of 6 : 1 or 3 : 1 (hostguest). The 'waist' of the hour-glass shape of the host cage 43 is a result of an R 6 6 ( 12) motif of O-H/O hydrogen bonds, Scheme 3.…”

Section: Christoph Janiakmentioning

confidence: 99%

Recent advances in crystal engineering

2010

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“…Among these, hydroquinone (or quinol) 67,68 and alicyclic alcohols 71,73 were shown to have meta-stable guest-free structures similar to that of Dianin's compound, having sometimes been classified in a common family of compounds. 72 Following Barrer's original work, it was only in 1991, with the work of Ung et al on polyalicyclic diols, that another organic inclusion compound was found to possess guest-free stable porosity, in a way that ''may be compared to those of inorganic zeolite lattices''. 70 Interestingly, these also possess an identical crystal structure and porous network to that of Dianin's compound.…”

Section: Organic Supramolecular Microporous Solidsmentioning

confidence: 99%

Peptide-based solids: porosity and zeolitic behavior

2012

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Among the greatest challenges in the field of microporous solids is the development of ''smart'' materials, displaying environment-triggered property tuning. These could be used both in traditional and new applications of microporous materials. In this context, supramolecular peptide-based solids have recently emerged as interesting alternatives to standard microporous solids, such as zeolites and carbon molecular sieves. They possess framework and conformational flexibility, are kinetically stable and reasonably thermally resistant. Important properties such as pore size and inner wall chemistry can be controlled through appropriate chemical modification of the peptide molecules. Peptide-based porous solids have permanent microporosity, often with molecularly sized cavities created by removal of co-crystallised solvent. Some have already been successfully tested as adsorbents and permselective materials, confirming their potential. This review covers the identification, synthesis, characterization techniques and properties of peptide-based microporous solids, discussing their most unique functionalities.

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Nodal equivalence of (O–H)6 and aromatic rings: a supramolecular cousin of Dianin's compound and β-hydroquinone1,2

Cited by 9 publications

References 25 publications

The Chemistry of Porous Organic Molecular Materials

The Chemistry of Porous Organic Molecular Materials

Recent advances in crystal engineering

Peptide-based solids: porosity and zeolitic behavior

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