Catenated and non-catenated inclusion complexes of trimesic acid

Herbstein, F. H.; Kapon, Moshe; Reisner, G. M.

doi:10.1007/bf00655650

Cited by 96 publications

(68 citation statements)

References 4 publications

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“…[3b, 5, 8] Although H 3 -2 itself forms two-dimensional infinite honeycomb grids, their pores are usually filled by interpenetration or catenation of other grids and thus extremely few uncatenated structures of H 3 -2 are reported in which the cavities are occupied by some organic guests. [9] Therefore, if 1 and 2 are self-assembled in water, each nickel(ii) macrocycle will interact with two units of 2 up and down with respect to its macrocyclic plane and each unit of 2 will interact with three nickel(ii) units since 2 contains three carboxylate groups. Based on this building scheme, the assembly will lead to a three-dimensional network.…”

mentioning

confidence: 99%

Self-Assembly of a Molecular Floral Lace with One-Dimensional Channels and Inclusion of Glucose

Choi

Lee

Suh

1999

Angew. Chem. Int. Ed.

217

111

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confidence: 99%

Self-Assembly of a Molecular Floral Lace with One-Dimensional Channels and Inclusion of Glucose

Choi

Lee

Suh

1999

Angew. Chem. Int. Ed.

217

111

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“…Such interpenetration (or catenation) is appreciated for its aesthetic appeal and offers potential host materials if guest molecules can be exploited to prevent interpenetration. 6 Understanding and predicting interpenetration patterns therefore constitutes an important aspect of crystal engineering.Self-assembly can be an effective strategy for crystal engineering but it requires careful control over molecular symmetry and functionality. 3 In general, tetrahedral molecules with rigid complementary hydrogen bonding sites adapt diamondoid architecture with levels of interpenetration based on the relative size of superdiamondoid cage and the volume of the tecton.…”

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confidence: 99%

A supramolecular carpet formed via self-assembly of bis(4,4′-dihydroxyphenyl) sulfone

Davies¹,

Langler²,

Sharma³

et al. 1997

Chem. Commun.

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Bis(4,4A-dihydroxyphenyl) sulfone 1 exploits its tetrahedrally disposed complementary hydrogen bonding sites to generate a unique doubly interwoven molecular carpet architecture in the solid state.The concept of rational design of 2D and 3D frameworks has evoked considerable interest in recent years as many functional properties of solids are dependent on crystal packing. 1,2 A particularly interesting and relevant problem that has been addressed by several groups concerns the preparation of open cage and/or interwoven networks. [3][4][5] While the former is desired in the context of porous solids, the latter is an associated phenomenon which invariably occurs if > 50% of a solid would otherwise be empty. Such interpenetration (or catenation) is appreciated for its aesthetic appeal and offers potential host materials if guest molecules can be exploited to prevent interpenetration. 6 Understanding and predicting interpenetration patterns therefore constitutes an important aspect of crystal engineering.Self-assembly can be an effective strategy for crystal engineering but it requires careful control over molecular symmetry and functionality. 3 In general, tetrahedral molecules with rigid complementary hydrogen bonding sites adapt diamondoid architecture with levels of interpenetration based on the relative size of superdiamondoid cage and the volume of the tecton. 7 We report herein an alternate motif for such compounds which occurs if there is flexibility present in the tecton: interwoven 2D square grids. 8 A solution of bis(4-chlorophenyl) sulfone (4.0 g) and sodium hydroxide (4.0 g) in Me 2 SO (160 ml) and water (40 ml) was maintained at 100 °C for two months. Extractive workup with diethyl ether furnished a mixture of unchanged chloro sulfone, bis(4-hydroxyphenyl) sulfone 1 and 4-chlorophenyl (4A-hydroxyphenyl) sulfone 2. Chloroform elution on silica gel furnished pure 1 (2%) and 2 (50%).Non-centrosymmetric crystals of 1 were obtained from acetone-CHCl 3 (mp 247-249 °C). The crystal structure ‡ reveals an infinite 2D hydrogen bonded network sustained by interaction between hydroxy and sulfone groups (O···O 2.705(7), 2.800(3) Å, Fig. 1). The network generates square cavities with ca. 8 3 10 Å dimensions, large enough to facilitate generation of a 2-fold interwoven molecular carpet (Fig. 2). The entangled 2D grids are stabilized by van der Waals and herringbone interactions. A 3D diamondoid architecture is also feasible but presumably packs less efficiently in the absence of an appropriate guest.The molecular carpet architecture of 1 demonstrates how molecules with flexible hydrogen bonding sites can selfassemble to yield 2D interwoven networks as an alternative to 3D diamondoid architectures. Such networks would be expected to have clay-like intercalation properties and, if appropriate guests can be used to eschew interpenetration, large cavities within the grid. 9 The critical importance of complementarity amongst the hydrogen bonding sites is illustrated by what happens if one hydroxy substituent of 1 is repl...

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“…In pure BTC, 37 threefold self-interpenetration of the hexagonal networks occurs with puckering of each honeycomb network, 11A (Figure 12a). When crystallized in the presence of small solvent molecules, BTC forms an open honeycomb structure with adjacent layers aligned to form small cavities capable of holding molecules such as halogens, 38 linear alkanes, 39 and p-nitroaniline 4 (11B, Figure 12b). …”

Section: Catananes or Interpenetrated Networkmentioning

confidence: 99%

Supramolecular Isomerism

Bourne¹

2012

Supramolecular Chemistry

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Supramolecular isomers comprise network structures that have identical chemical compositions but differ from one another in their structure. In some instances, the term is also used to describe identical frameworks that contain different counterions, solvent, or guest molecules. Supramolecular isomerism can be observed in both molecular and coordination compounds. Like polymorphism, it results when different, but energetically similar, packing interactions can operate during crystallization. Gaining control on crystallization of a particular isomer remains challenging as both thermodynamic and kinetic factors play a role, and as understanding the full energy profile of a self‐assembly process is extremely difficult. Some important variables within the crystallization system have been identified, including chemical and physical factors, which are described in this chapter. Supramolecular isomers may be considered in four categories: structural, conformational, interpenetrated, and chiral networks. Examples of each are provided. A number of topological approaches have been described over the years, which aid in the description of extended structures. Both graph set and network analyses are useful for this purpose. Crystal engineering aims to control structural characteristics of crystalline materials, with the aim of having greater control over their physical properties. Although hydrogen‐bonded supramolecular synthons have been studied in depth for more than a decade and although coordination bonds are stronger and more directional than other supramolecular interactions, structural uncertainty is still a characteristic of self‐assembled systems. Some structure‐property relationships are emerging, including luminescence and porosity.

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Catenated and non-catenated inclusion complexes of trimesic acid

Cited by 96 publications

References 4 publications

Self-Assembly of a Molecular Floral Lace with One-Dimensional Channels and Inclusion of Glucose

Self-Assembly of a Molecular Floral Lace with One-Dimensional Channels and Inclusion of Glucose

A supramolecular carpet formed via self-assembly of bis(4,4′-dihydroxyphenyl) sulfone

Supramolecular Isomerism

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