The Sulfur Hexafluoride Clathrate of Dianin's Compound (4-p-Hydroxyphenyl-2,2,4-trimethylchroman): Preparation, Characterization and Thermal Decomposition

Mandelcorn, L.; Goldberg, Norman; Hoff, R. E.

doi:10.1021/ja01498a016

Cited by 5 publications

(3 citation statements)

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“…The very first porous H-bonded extended organic frameworks were made by Dianin in 1914, 40 years earlier than the discovery of the DNA double-helix crystal structure by Wason and Crick . The gas adsorption behavior of Dianin’s compounds was uncovered later, in the 1960s, − when it was reported that a large number of guests could be included within its trigonal crystal structures . Hughes reported the crystal structures of cyanamide dimers and trimers in the 1940s (Figure ).…”

Section: History Of Hofsmentioning

confidence: 99%

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

et al. 2022

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Hydrogen-bonded organic frameworks (HOFs), self-assembled from strategically pre-designed molecular tectons with complementary hydrogen-bonding patterns, are rapidly evolving into a novel and important class of porous materials. In addition to their common features shared with other functionalized porous materials constructed from modular building blocks, the intrinsically flexible and reversible H-bonding connections endow HOFs with straightforward purification procedures, high crystallinity, solution processability, and recyclability. These unique advantages of HOFs have attracted considerable attention across a broad range of fields, including gas adsorption and separation, catalysis, chemical sensing, and electrical and optical materials. However, the relatively weak H-bonding interactions within HOFs can potentially limit their stability and potential use in further applications. To that end, this Perspective highlights recent advances in the development of chemically and thermally robust HOF materials and systematically discusses relevant design rules and synthesis strategies to access highly stable HOFs.

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Section: History Of Hofsmentioning

confidence: 99%

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

et al. 2022

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“…109 Dianin's compound and the lower limit of nanoporosity Inclusion compounds from 4-(4 0 -hydroxyphenyl)-2,2,4-trimethylchroman 2 have been recognised since Dianin's original research published in 1914 110 and they have played an important role in the early studies of such materials due to the very large number of included guests that can be accommodated within its trigonal crystal structure. 30,[111][112][113] The crystal structures of ICs of 2 are remarkably invariant and are composed of a columnar arrangement of cages each formed by six host molecules held together by hydrogen-bonding. The void within the cage is hourglass-shaped with a maximum length of 11 A and maximum and minimum diameters of 6.5 and 4.4…”

Section: The 'Burden Of Proof' For Nanoporous Molecular Crystalsmentioning

confidence: 99%

Nanoporous molecular crystals

2010

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Nanoporous Molecular Crystals (NMCs) are nanoporous materials composed of discrete molecules between which there are only non-covalent interactions-i.e. they do not possess an extended framework composed of covalent or coordination bonds. They are formed from removing guest molecules from inclusion compounds (ICs) a process that for most ICs usually results in the collapse of the open structure of the crystals but in the case of NMCs the packing of the host molecules is retained and nanoporosity obtained. In recent years a number of NMCs have been confirmed by the technique of gas adsorption and these materials are surveyed in this feature article. In addition, the reasons for stability of these crystals are discussed. It is the author's belief that many more ICs, the structures of which are readily obtainable from the Cambridge Structural Database (CSD), may act as precursors to NMCs.

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“…Although organic clathrates were regarded as fascinating scientific curiosities since the 19th century, 4 they retained attention for their potential interest in various practical interesting applications such as gas separation by selective clathration, 5,6 lubrication and fuel additives, 7 or stabilization of unstable molecules and storage of toxic compounds. [8][9][10] Among the various organic hosts, hydroquinone or 1,4-benzenediol (denoted HQ in the following) is a hydroxyphenolic organic compound of formula C 6 H 6 O 2 . HQ presents three usual polymorphic forms in the solid state (a, b and g).…”

Section: Introductionmentioning

confidence: 99%

Revisiting the thermodynamic modelling of type I gas–hydroquinone clathrates

Conde

Torré

Miqueu

2016

Phys. Chem. Chem. Phys.

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Under specific pressure and temperature conditions, certain gaseous species can be engaged in a host lattice of hydroquinone molecules, forming a supramolecular entity called a gas hydroquinone clathrate. This study is devoted to the thermodynamic modelling of type I hydroquinone clathrates. The gases considered in this work are argon, krypton, xenon, methane, nitrogen, oxygen and hydrogen sulphide. The basic van der Waals and Platteeuw model, which is, for example, not able to predict well the phase equilibrium properties of such clathrates at high temperature, is modified and extended by considering first the solubility of the guest in solid HQ and then the mutual interactions between the gaseous molecules inside the clathrate structure (i.e. guest-guest interactions). Other improvements of the basic theory, such as the choice of the reference state, are proposed, and a unique set of thermodynamic parameters valid for all the studied guests are finally calculated. Very good agreement is obtained between the model predictions and the experimental data available in the literature. Our results clearly demonstrate that the highest level of theory is necessary to describe well both the triphasic equilibrium line (where the HQ clathrate, the native hydroquinone HQα and the gas coexist), the occupancy of the guest in the clathrate, and the intercalation enthalpy.

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The Sulfur Hexafluoride Clathrate of Dianin's Compound (4-p-Hydroxyphenyl-2,2,4-trimethylchroman): Preparation, Characterization and Thermal Decomposition

Cited by 5 publications

References 0 publications

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

Design Rules of Hydrogen-Bonded Organic Frameworks with High Chemical and Thermal Stabilities

Nanoporous molecular crystals

Revisiting the thermodynamic modelling of type I gas–hydroquinone clathrates

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