Controlled Expansion of a Molecular Cavity in a Steroid Host Compound

Sada, Kazuki; Sugahara, Michihiro; Katō, K.; Miyata, Mikiji

doi:10.1021/ja0038528

Cited by 53 publications

(35 citation statements)

References 39 publications

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“…On the other hand, the elongation of the side-chain may give rise to expansion of the host cavity. In fact, If, which has longer side-chain length by two methylene units than Ia, form inclusion compounds with larger aromatic compounds, such as 1-methylnaphthalene in a 1:1 host-to-guest ratio [ Figure 2(f)] [55]. Epimerization at the 3-position alters the inclusion abilities due to a change of the direction of the hydroxyl group [56].…”

Section: Hosts With Different Side-chain Length and Reversed Hydroxylmentioning

confidence: 99%

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

2007

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Abstract:Steroidal bile acids and their derivatives exhibit characteristic inclusion behaviors in the crystalline state. Their crystals present varied assemblies due to asymmetric molecular structures, which relate to supramolecular properties through cooperative weak interactions. An overview indicates that the steroidal assemblies lie in an intermediate position among various molecules and have hierarchical structures such as primary, secondary, tertiary, and host-guest assemblies like proteins. Such an interpretation brought about the idea that the assemblies with dimensionality present supramolecular chirality such as three-axial, tilt, helical, bundle, and complementary chirality. This concept of the supramolecular chirality enables us to understand formation of chiral crystals starting from the molecular chirality of the steroidal molecules.

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Section: Hosts With Different Side-chain Length and Reversed Hydroxylmentioning

confidence: 99%

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

2007

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“…This knowledge can be very useful for the proposition of the structure of BS aggregates in aqueous solution, a strategy firstly and largely employed by Giglio and coworkers [31], and of the supramolecular structures of BS derivatives [32]. Miyata et al [33][34][35][36] have carried out studies on BA crystals in a large variety of solvents and guests, also systematically modified the steroid structure. It can be concluded from these studies that the solid state structure depends on subtle differences in donor-acceptor relationships among the hydrogen bonding groups of guest and steroid molecules.…”

Section: R1mentioning

confidence: 99%

A Standard Structure for Bile Acids and Derivatives

et al. 2018

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Abstract:The crystal structures of two ester compounds (a monomer in its methyl ester form, with an amino isophthalic group, and a dimer in which the two steroid units are linked by a urea bridge recrystallized from ethyl acetate/methanol) derived from cholic acid are described. Average bond lengths and bond angles from the crystal structures of 26 monomers and four dimers (some of them in several solvents) of bile acids and esters (and derivatives) are used for proposing a standard steroid nucleus. The hydrogen bond network and conformation of the lateral chain are also discussed. This standard structure was used to compare with the structures of both progesterone and cholesterol.

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“…A limited number of organic crystals have been reported as the organic mimics of clay. [142][143][144][145][146][147][148] Intercalation chemistry is important to develop advanced materials such as heterogeneous catalysts, ionic and protonic conductors, specific adsorbents, nonlinear optics, photonic devices, and nanocomposites.…”

Section: Materials Design By Organic Intercalationmentioning

confidence: 99%

Polymer Structure Control Based on Crystal Engineering for Materials Design

Matsumoto

2003

Polym J

111

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ABSTRACT:In this review article, polymer structure control and organic material design based on polymer crystal engineering are described. The structures and properties of crystalline materials are designed using pre-organized molecules through various intermolecular interactions such as hydrogen bonds, π · · · π, CH/π, CH/O, and halogen interactions. Here, we describe the features and mechanisms of the topochemical polymerization of 1,3-diene monomers including some ester, ammonium, and amide derivatives of muconic and sorbic acids, which are 1,3-diene di-and monocarboxylic acid derivatives, respectively. We have proposed the topochemical polymerization principles for diene monomers on the basis of the crystallographic data accumulated for various kinds of diene monomers. The combination of several intermolecular interactions is useful for the construction of molecular packing appropriate for 5 Å stacking in order to facilitate the topochemical polymerization in the crystalline state. We refer to the control of polymer chain structure including tacticity, molecular weight, and ladder structure, and also polymer crystal structures, as well as the organic intercalation system using layered polymer crystals obtained by the topochemical polymerization. A totally solvent-free system for the synthesis of layered polymer crystals is also described.KEY WORDS Topochemical Polymerization / Solid-State Reaction / Crystal Engineering / Supramolecular Synthon / Stereoregular Polymer / Controlled Radical Polymerization / X-Ray Single Crystal Structure Analysis / Intercalation / Controlled polymer synthesis, including the control of polymer chain structures such as molecular weight, molecular weight distribution, chain-end structure, branching, regioselectivity, and stereoselectivity, has great potential for the design of macromolecular architecture leading to advanced nano-materials and devices. [1][2][3][4][5][6][7][8][9][10][11] All the features and functions of polymers importantly depend on primary chain structures and the manner of polymer chain assembly in crystalline and non-crystalline solids, or in a condensed state. Therefore, the control of polymer chain structures in polymer synthesis can hardly be overestimated for the architecture of advanced polymeric materials.Especially, the stereochemistry of polymers has received significant attention in both fundamental and applied fields ever since the first discoveries of stereoregular polymers in the 1950s. 12-14 Highly controlled stereospecific polymerization has been well established by coordination polymerization of olefins and diene monomers and by anionic polymerization of certain types of polar monomers. Radical polymerization is the most important and convenient process for the production of various kinds of vinyl and diene polymers due to recent achievements in well-controlled polymerizations in addition to the classical advantages of the radical process. [15][16][17][18][19][20][21][22] There are two fundamentally different ways to control of the chain structu...

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Controlled Expansion of a Molecular Cavity in a Steroid Host Compound

Cited by 53 publications

References 39 publications

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

Supramolecular Chirality in Crystalline Assemblies of Bile Acids and Their Derivatives; Three-Axial, Tilt, Helical, and Bundle Chirality

A Standard Structure for Bile Acids and Derivatives

Polymer Structure Control Based on Crystal Engineering for Materials Design

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