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Superstructures with cyclodextrins: Chemistry and applications


Editor: Prof. Helmut Ritter
Heinrich-Heine-Universität Düsseldorf

Cyclodextrins (CDs) are cyclic oligosaccharides consisting of 1,4-glycosidically linked α-D-glucose units. Production of these compounds is accomplished by enzymatic degradation of starch using CD-glycosyl transferase. Since their discovery more than 100 years ago, a significant development in CD research has taken place. Various applications of CDs can be found, e.g. the binding of odors and flavors. Even drugs can be complexed and set free after a while by CDs. This enables the transfer of hydrophobic substances into aqueous media, which is of great interest in pharmaceutical chemistry. Regarding the interactions of CDs with low-molecular and macromolecular compounds, respectively, the reactivity of complexed molecules is another key factor besides solubility effects.

In organic synthesis and polymer chemistry, the interest in CDs has increased significantly during the past decades. For instance, in the latter case covalent attachment of CDs to macromolecules and threading of CD molecules onto suitable macromolecular chains could be demonstrated. Unlike other macrocycles such as crown ethers or calixarenes, the cavity of CDs is big enough to include more or less hydrophobic molecules completely.



 
Overview

Superstructures with cyclodextrins: Chemistry and applications

Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1303–1304. published 16 Aug 2012

Editorial

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

Wenting Liang, Cheng Yang, Masaki Nishijima, Gaku Fukuhara, Tadashi Mori, Andrea Mele, Franca Castiglione, Fabrizio Caldera, Francesco Trotta, Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311. published 16 Aug 2012

Letter

Interaction of cyclodextrins with pyrene-modified polyacrylamide in a mixed solvent of water and dimethyl sulfoxide as studied by steady-state fluorescence

Akihito Hashidzume, Yongtai Zheng, Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1312–1317. published 16 Aug 2012

Full Research Paper

Restructuring polymers via nanoconfinement and subsequent release

Alan E. Tonelli

Beilstein J. Org. Chem. 2012, 8, 1318–1332. published 16 Aug 2012

Review

Impact of cyclodextrins on the behavior of amphiphilic ligands in aqueous organometallic catalysis

Hervé Bricout, Estelle Léonard, Christophe Len, David Landy, Frédéric Hapiot, Eric Monflier

Beilstein J. Org. Chem. 2012, 8, 1479–1484. published 06 Sep 2012

Full Research Paper

Synthesis and characterization of low-molecular-weight π-conjugated polymers covered by persilylated β-cyclodextrin

Aurica Farcas, Ana-Maria Resmerita, Andreea Stefanache, Mihaela Balan, Valeria Harabagiu

Beilstein J. Org. Chem. 2012, 8, 1505–1514. published 11 Sep 2012

Full Research Paper

Influence of cyclodextrin on the solubility of a classically prepared 2-vinylcyclopropane macromonomer in aqueous solution

Helmut Ritter, Jia Cheng, Monir Tabatabai

Beilstein J. Org. Chem. 2012, 8, 1528–1535. published 13 Sep 2012

Full Research Paper

Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition

Ulrike Kauscher, Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551. published 17 Sep 2012

Full Research Paper

Supramolecular hydrogels formed from poly(viologen) cross-linked with cyclodextrin dimers and their physical properties

Yoshinori Takashima, Yang Yuting, Miyuki Otsubo, Hiroyasu Yamaguchi, Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1594–1600. published 20 Sep 2012

Full Research Paper

Polysiloxane ionic liquids as good solvents for β-cyclodextrin-polydimethylsiloxane polyrotaxane structures

Narcisa Marangoci, Rodinel Ardeleanu, Laura Ursu, Constanta Ibanescu, Maricel Danu, Mariana Pinteala, Bogdan C. Simionescu

Beilstein J. Org. Chem. 2012, 8, 1610–1618. published 24 Sep 2012

Full Research Paper

Molecular solubilization of fullerene C60 in water by γ-cyclodextrin thioethers

Hai Ming Wang, Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1644–1651. published 28 Sep 2012

Full Research Paper

Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles

Ângelo M. L. Denadai, Frederico B. De Sousa, Joel J. Passos, Fernando C. Guatimosim, Kirla D. Barbosa, Ana E. Burgos, Fernando Castro de Oliveira, Jeann C. da Silva, Bernardo R. A. Neves, Nelcy D. S. Mohallem, Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876. published 01 Nov 2012

Full Research Paper

Influence of intramolecular hydrogen bonds on the binding potential of methylated β-cyclodextrin derivatives

Gerhard Wenz

Beilstein J. Org. Chem. 2012, 8, 1890–1895. published 06 Nov 2012

Full Research Paper

Cyclodextrin-induced host–guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

Gero Maatz, Arkadius Maciollek, Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935. published 14 Nov 2012

Full Research Paper

Cyclodextrin-based nanosponges as drug carriers

Francesco Trotta, Marco Zanetti, Roberta Cavalli

Beilstein J. Org. Chem. 2012, 8, 2091–2099. published 29 Nov 2012

Review

New enzymatically polymerized copolymers from 4-tert-butylphenol and 4-ferrocenylphenol and their modification and inclusion complexes with β-cyclodextrin

Adam Mondrzyk, Beate Mondrzik, Sabrina Gingter, Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123. published 04 Dec 2012

Full Research Paper

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton® X-100

Melanie Kemnitz, Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183. published 13 Dec 2012

Full Research Paper

Theoretical study on β-cyclodextrin inclusion complexes with propiconazole and protonated propiconazole

Adrian Fifere, Narcisa Marangoci, Stelian Maier, Adina Coroaba, Dan Maftei, Mariana Pinteala

Beilstein J. Org. Chem. 2012, 8, 2191–2201. published 17 Dec 2012

Full Research Paper

Inclusion of the insecticide fenitrothion in dimethylated-β-cyclodextrin: unusual guest disorder in the solid state and efficient retardation of the hydrolysis rate of the complexed guest in alkaline solution

Dyanne L. Cruickshank, Natalia M. Rougier, Raquel V. Vico, Susan A. Bourne, Elba I. Buján, Mino R. Caira, Rita H. de Rossi

Beilstein J. Org. Chem. 2013, 9, 106–117. published 17 Jan 2013

Full Research Paper

The β-cyclodextrin/benzene complex and its hydrogen bonds – a theoretical study using molecular dynamics, quantum mechanics and COSMO-RS

Jutta Erika Helga Köhler, Nicole Grczelschak-Mick

Beilstein J. Org. Chem. 2013, 9, 118–134. published 18 Jan 2013

Full Research Paper

Superstructures of fluorescent cyclodextrin via click-reaction

Arkadius Maciollek, Helmut Ritter, Rainer Beckert

Beilstein J. Org. Chem. 2013, 9, 827–831. published 29 Apr 2013

Full Research Paper

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

Sophie Fourmentin, Anca Ciobanu, David Landy, Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191. published 19 Jun 2013

Full Research Paper

Linkage of α-cyclodextrin-terminated poly(dimethylsiloxanes) by inclusion of quasi bifunctional ferrocene

Helmut Ritter, Berit Knudsen, Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284. published 01 Jul 2013

Full Research Paper

Topochemical control of the photodimerization of aromatic compounds by γ-cyclodextrin thioethers in aqueous solution

Hai Ming Wang, Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1858–1866. published 12 Sep 2013

Full Research Paper

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

Julian Fischer, Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811. published 05 Dec 2013

Full Research Paper

N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation

Julian Fischer, Simon Millan, Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2834–2840. published 09 Dec 2013

Full Research Paper