Guest-responsive structural changes in cholic acid intercalation crystals

Miyata, Mikiji; Shibakami, Motonari; Chirachanchai, Suwabun; Takemoto, Kiichi; Kasai, Nobutami; Miki, Kunio

doi:10.1038/343446a0

Cited by 110 publications

(46 citation statements)

References 5 publications

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“…It should be emphasized that this ability to adopt a variety of crystal forms found only in CA may be of a quite different nature from that in DCA, because DCA includes various organic guest molecules in a similar molecular arrangement with space group P2~2~2~. In addition, we have found intercalation phenomena for this CA crystal when soaking in some organic solvents (Miyata, Shibakami, Chirachanchai, Takemoto, Kasai & Miki, 1990). This is also a specific ability observed only in CA crystals.…”

Section: =mentioning

confidence: 56%

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Crystal structure of cholic acid with no guest molecules

Miki¹,

Kasai²,

Shibakami³

et al. 1990

Acta Crystallogr C

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Section: =mentioning

confidence: 56%

“…The present struc-c(23) 0-4312 ture was reported in part by Miyata,Shibakami,c(24) 0.3841 Chirachanchai, Takemoto, Kasai & Miki (1990). Direct methods using SHELXS86 (Sheldrick, 1986) were employed for the structure solution, which found all 29 non-H atoms.…”

Section: =mentioning

confidence: 99%

Crystal structure of cholic acid with no guest molecules

Miki¹,

Kasai²,

Shibakami³

et al. 1990

Acta Crystallogr C

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“…This is favorable for seeking a chirality linkage among the hierarchical structures in universe [54,55], where supramolecular chirality in crystals are significant as one of the expression of molecular information [3,4,8,10]. The 21 helical columns seem to be analogous to 3D building-bricks in daily life, inducing a delightful research in crystal engineering toward creation of chiral materials, including organic, inorganic and polymeric compounds, starting from achiral components.…”

Section: Discussionmentioning

confidence: 99%

“…Since the discovery of cholic acid inclusion compounds [1][2][3], our research has been devoted to supramolecular chirality in crystals of chiral molecules, such as steroids [4][5][6][7][8][9][10] and alkaloids [11][12][13][14][15][16][17][18]. The fascinating relations between molecules and their assemblies gradually directed us toward achiral molecules.…”

Section: Introductionmentioning

confidence: 99%

Generation of Supramolecular Chirality around Twofold Rotational or Helical Axes in Crystalline Assemblies of Achiral Components

et al. 2015

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A multi-point approximation method clarifies supramolecular chirality of twofold rotational or helical assemblies as well as bundles of the one-dimensional (1D) assemblies. While one-point approximation of materials claims no chirality generation of such assemblies, multi-point approximations do claim possible generation in the 1D assemblies of bars and plates. Such chirality derives from deformations toward three-axial directions around the helical axes. The chiral columns are bundled in chiral ways through symmetry operations. The preferable right-or left-handed columns are bundled together to yield chiral crystals with right-or left-handedness, respectively, indicating that twofold helix symmetry operations cause chiral crystals composed of achiral components via a three-stepwise and three-directional process.

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“…[12][13][14][15] In contrast to a large number of studies on intercalation systems made of inorganic compounds or inorganic-organic hybrids, very few examples are known as an intercalation system consisting of organic compounds as both the host and guest. [16][17][18][19][20][21] We have previously demonstrated the fundamental features and mechanism of the intercalation of various alkylamines into poly(muconic acid) (PMA) as the organic host compound [21][22][23][24] (Scheme 1). Long-chain alkylamines are suitable as the guest molecules and the intercalation provides a new layered polymer crystal with an interlayer spacing different from that of the original PMA crystals.…”

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confidence: 99%

Organic Intercalation of Unsaturated Amines into Layered Polymer Crystals and Solid-State Photoreactivity of the Guest Molecules in Constrained Interlayers

Matsumoto

Fujioka

Kunisue

2003

Polym J

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ABSTRACT:We have investigated the intercalation of several unsaturated amines using poly(muconic acid) crystals as the layered organic polymer host. Allyl-and oleylamines are intercalated into the polymer crystals in order to introduce an olefin moiety in the side chain of poly(muconic acid). The oleylammonium polymer crystals are alternatively obtained by the topochemical polymerization of oleylammonium muconate as the corresponding ammonium monomer crystals under photoirradiation in the crystalline state, while the photoirradiation of the allylammonium muconate crystals results in the formation of isomers. The inner double bond of the intercalated oleyl group has a low reactivity under UV irradiation, and the allyl group has no reactions. In contrast, diene and diyne moieties introduced into the side chain by the intercalation using 2,4-hexadienyl-, 2,4-tetradecyldienyl-, and 10,12-pentacosadiynylamines as the guest amines readily react to give a new type of the polymer crystal consisting of alternately stacked polymer nano-sheets. We have revealed that the intercalation of long-chain unsaturated amines proceeds in a high conversion, and the photoreactivity of the unsaturated functional groups in the side chain is determined by the kind of unsaturated groups and the stacking distance of the amine molecules in the layers.KEY WORDS Layered Polymer Crystals / Intercalation / Poly(muconic acid) / Solid-State Photoreaction / Polydiacetylene / Organic/inorganic nano-composites with an organized structure have attracted interests in the fundamental and applied fields of polymer chemistry and nanomaterial science. 1-3 A large number of inorganic solids with a two-dimensional structure such as clays, metal phosphonates or phosphites, graphite, and metal oxides have been reported, 4, 5 and the properties and functions of these layered materials are modified by combination with organic molecules as the guest compounds. [6][7][8][9][10][11] The combination of materials with a different nature efficiently induces a new property and function, which cannot be attained from an organic or inorganic compound alone. The structure and properties of the composites consisting of various types of clays and polymers have also been investigated. [12][13][14][15] In contrast to a large number of studies on intercalation systems made of inorganic compounds or inorganic-organic hybrids, very few examples are known as an intercalation system consisting of organic compounds as both the host and guest. [16][17][18][19][20][21] We have previously demonstrated the fundamental features and mechanism of the intercalation of various alkylamines into poly(muconic acid) (PMA) as the organic host compound 21-24 (Scheme 1). Long-chain alkylamines are suitable as the guest molecules and the intercalation provides a new layered polymer crystal with an interlayer spacing different from that of the original PMA crystals. The organic intercalation system consisting of layered organic polymers and organic guest amines has some characteristics different fr...

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Guest-responsive structural changes in cholic acid intercalation crystals

Cited by 110 publications

References 5 publications

Crystal structure of cholic acid with no guest molecules

Crystal structure of cholic acid with no guest molecules

Generation of Supramolecular Chirality around Twofold Rotational or Helical Axes in Crystalline Assemblies of Achiral Components

Organic Intercalation of Unsaturated Amines into Layered Polymer Crystals and Solid-State Photoreactivity of the Guest Molecules in Constrained Interlayers

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