A Homologous Series of Persubstituted Cyclodextrin Amino Acids: The Quest for Tubular Self‐Assembly

Kraus, Tomáš; Budêšínský, Miloś; Cı́sařová, Ivana; Závada, Jiřı́

doi:10.1002/ejoc.200400272

Cited by 14 publications

(9 citation statements)

References 36 publications

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“…Although the aqueous reaction mixture became transparent, the 1 H NMR spectra of the collected sample suggested considerable decomposition of most CD moieties. This was due to the competing oxidation of C‐2 and C‐3 secondary hydroxyl groups to keto groups, which occurs only in the case of CD oxidation by TEMPO,69 and further decomposition of the CDs by the excess addition of sodium hypochlorite, the co‐oxidant.…”

Section: Resultsmentioning

confidence: 99%

Polyrotaxane derivatives. II. Preparation and characterization of ionic polyrotaxanes and ionic slide‐ring gels

Araki

2011

J. Polym. Sci. A Polym. Chem.

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Four types of ionic polyrotaxane (PR) derivatives, that is, carboxymethylated, sulfoethylated, diethylaminoethylated, and trimethylammoniohydroxypropylated PRs, were successfully prepared starting from the same PR consisting of poly(ethylene glycol) as an axis and a-cyclodextrins as ring molecules. The structures of the ionic PR derivatives were analyzed by 1 H and 13 C nuclear magnetic resonance (NMR), attenuated-total reflection Fourier transform-infrared, and colloidal titration. Degrees of substitution of the ionic PRs were calculated from results of 1 H NMR and colloidal titrations; both sets of results satisfactorily agreed. Cross-linking of sulfoethylated and quaternized PRs yielded ionic slide-ring gels carrying sulfoethyl and quaternary ammonium groups on the mobile cross-links, respectively. The former gel showed intriguing phenomena, including a large degree of swelling of up to 1147, drastic change in its swelling ratio by the presence of electrolyte and bending under a moderate applied electric field (7 V/cm).

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Section: Resultsmentioning

confidence: 99%

Polyrotaxane derivatives. II. Preparation and characterization of ionic polyrotaxanes and ionic slide‐ring gels

Araki

2011

J. Polym. Sci. A Polym. Chem.

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“…[28] The "three-point rule" states that at least three directed interactions between host and guests are prerequisites for noticeable chiral discrimination. [29] In addition, hepta-6-, [24] hepta-2,3-di-, [30] hepta-2,6-di-, [31] and hepta-2,3,6trisubstituted [32][33][34] b-CD derivatives have been synthesized. In particular, hepta-6-S-6-deoxy-b-CD derivatives, [35][36][37][38] which are readily synthesized from heptakis-6-iodo-6-deoxyb-CD and functional thiols, show interesting binding properties.…”

Section: Introductionmentioning

confidence: 99%

Recognition of Ionic Guests by Ionic β‐Cyclodextrin Derivatives

Wenz

Strassnig

Thiele

et al. 2008

Chemistry A European J

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Inclusion compounds of cationic, anionic, and neutral p-substituted derivatives of tert-butylbenzene complexed in beta-cyclodextrin and its ionic 6-mono and 6-hepta derivatives were systematically investigated by isothermal titration calorimetry (ITC). All inclusion compounds showed 1:1 stoichiometry with binding constants ranging from 10 to 3 x 10(6) M(-1). The binding free energies could be subdivided into apolar and electrostatic contributions. The electrostatic interactions could be quantitatively described by Coulomb's law by taking into account the degree of protonation of hosts and guests, the orientations of the guests within the hosts, and ion shielding as described by the Debye-Hückel-Onsager theory. The orientations of the guests within the cyclodextrin cavities were determined by ROESY NMR spectroscopy.

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“…The series of bipyridylamide‐cyclodextrin derivatives 1 a – 1 c was obtained by the condensation of per(5‐carboxy‐5‐dehydroxymethyl)‐cyclodextrins [34] and 5‐amino‐5′‐methyl‐2,2′‐bipyridine (Figures S1–S16, Schemes S1–S6). Next, Fe(OTf) 2 (1 equiv) reacted with 1 a – 1 c (Figure 2 a).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Single Isomeric Complexes with Dissymmetric Structures Using Macrocyclic Homooligomers

et al. 2020

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Bottom‐up chemical synthesis to construct intricate molecules has been a profound challenge. An effective approach is to utilize organic ligands and metal ions, but the formation of a single product among other possible candidates has proven difficult for dissymmetric structures. We now report the synthesis of single isomeric complexes with dissymmetric structures using the mismatch in the coordination valences of macrocyclic homooligomers and metal ions. A series of amide‐cyclodextrin derivatives possessing multiple 2,2′‐bipyridyl (bpy) groups forms mononuclear complexes whose specific three bpy groups are linked in the fac‐Λ configuration. The intermolecular coordination of the β‐cyclodextrin metal complex produces a dissymmetric cyclodextrin trimer as a single isomer, whose initially equivalent 21 (=7×3) bipyridylamide‐pyranose units are placed in different environments. Furthermore, we realize chiral recognition of amino acid anions utilizing the distinctive amide groups arranged on the unsymmetrically fixed scaffold.

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A Homologous Series of Persubstituted Cyclodextrin Amino Acids: The Quest for Tubular Self‐Assembly

Cited by 14 publications

References 36 publications

Polyrotaxane derivatives. II. Preparation and characterization of ionic polyrotaxanes and ionic slide‐ring gels

Polyrotaxane derivatives. II. Preparation and characterization of ionic polyrotaxanes and ionic slide‐ring gels

Recognition of Ionic Guests by Ionic β‐Cyclodextrin Derivatives

Synthesis of Single Isomeric Complexes with Dissymmetric Structures Using Macrocyclic Homooligomers

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