Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

• Christina Lohoelter,
• Malte Brutschy,
• Daniel Lubczyk and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

• ; triptycenes; templates; Introduction Divalent building blocks with a well-defined geometry play a significant role in the construction of highly potent supramolecular structures [1][2][3][4][5]. The rigid nature of such architectures limits the degrees of freedom and guarantees a good preorganization [1][2

Bis(benzylamine) monomers: One-pot preparation and application in dendrimer scaffolds for removing pyrene from aqueous environments

• Olivia N. Monaco,
• Sarah C. Tomas,
• Meghan K. Kirrane and
• Amy M. Balija

Beilstein J. Org. Chem. 2013, 9, 2320–2327, doi:10.3762/bjoc.9.266

• to play an important role. Current efforts are focused on incorporating the bisamine dendron motif into additional supramolecular structures such as star polymers and hyperbranched systems and examining how fine-tuning the steric and electronic nature of the bisamine AB2 monomers influences the

Self-assembly of 2,3-dihydroxycholestane steroids into supramolecular organogels as a soft template for the in-situ generation of silicate nanomaterials

• Valeria C. Edelsztein,
• Andrea S. Mac Cormack,
• Matías Ciarlantini and
• Pablo H. Di Chenna

Beilstein J. Org. Chem. 2013, 9, 1826–1836, doi:10.3762/bjoc.9.213

• , electrochemistry, light-harvesting materials and so on [1][2][3][4][5][6]. These small molecules self-assemble into regular supramolecular structures through non covalent interactions such as ion–ion, dipole–dipole, hydrogen bonding, π–π stacking, van der Waals, host–guest, and ion coordination, and in so doing

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

• Helmut Ritter,
• Berit Knudsen and
• Valerij Durnev

Beilstein J. Org. Chem. 2013, 9, 1278–1284, doi:10.3762/bjoc.9.144

• supramolecular structures are hereby established. Thin-layer chromatography studies (toluene/ethanol 30:1 by volume) also indicate the presence of enclosed ferrocene in the cavity of the cyclodextrins. UV-active areas can be detected, which do not migrate with the solvent front in contrast to pure ferrocene

• the derivatives mechanically. In addition, the successful complexation of the α-CD-modified siloxanes and the formation of supramolecular structures via inclusion complexes with ferrocene can be illustrated in the TEM images of 4 (Figure 5). Figure 5A (α-CD-disiloxane 4) shows a majority of globular

• comparison to the uncomplexed educts, which is not influenced decisively by the presence of the smaller supramolecular structures. However, the peak at about 5000 nm indicates the presence of larger linear structures based on the complexation of α-CD-disiloxane 4 with the ferrocene molecules, which were also

Enhancement of efficiency in organic photovoltaic devices containing self-complementary hydrogen-bonding domains

• Rohan J. Kumar,
• Jegadesan Subbiah and
• Andrew B. Holmes

Beilstein J. Org. Chem. 2013, 9, 1102–1110, doi:10.3762/bjoc.9.122

• maintained by introduction of alkyl substituents at the β-position of the thiophenes, and the NH-cyanopyridone unit could be unmasked for hydrogen-bonding. In turn, this may allow access to higher order supramolecular structures, promoting charge transport and increasing the fill factor and efficiency of

Superstructures of fluorescent cyclodextrin via click-reaction

• Arkadius Maciollek,
• Helmut Ritter and
• Rainer Beckert

Beilstein J. Org. Chem. 2013, 9, 827–831, doi:10.3762/bjoc.9.94

• )-interactions. The supramolecular structures were characterized by 1H NMR-ROESY spectroscopy, dynamic light scattering, UV–vis spectroscopy, fluorescence spectroscopy, and asymmetric flow field-flow fractionation. By adding potassium adamantane-1-carboxylate, the thiazol dye is displaced from the CD-cavity and

• NOE interaction between protons of the methyl group of the thiazole and the triazole proton itself with CD is noticed. This indicates that only the inclusion of the pyridine moiety in the hydrophobic cavity of the CD takes place. The formation of supramolecular structures was also proven by UV–vis

• ]. To investigate the expected intermolecular formation of supramolecular structures in aqueous solution, dynamic light scattering (DLS) experiments were performed (Figure 4). Hydrodynamic diameters up to 200 nm indicate the postulated formation of intermolecular complexes. Thus, repeating complexation

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

• Jutta Erika Helga Köhler and
• Nicole Grczelschak-Mick

Beilstein J. Org. Chem. 2013, 9, 118–134, doi:10.3762/bjoc.9.15

• many inclusion complexes and remarkable influence on reactions, catalysis and supramolecular structures. Crystal structure of heptakis(6-O-triisopropylsilyl)-β-cyclodextrin benzene pyrene solvate; [C105H210O35Si7,0.5(C16H10),3.5(C6H6)], taken from The Cambridge Crystallographic Data Centre CCDC [9

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 and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2118–2123, doi:10.3762/bjoc.8.238

• addition, hydrodynamic diameters also indicate strongly that supramolecular structures were formed (Figure 2). The hydrodynamic diameter of copolymer 5 (7 nm) in DMF is much smaller than the value of the cyclodextrin-modified copolymer 7 (70 nm). After breaking of supramolecular structures by addition of

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

• Gero Maatz,
• Arkadius Maciollek and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935, doi:10.3762/bjoc.8.224

• , reversible complexation [1][2][3][10][11]. In recent years, increasing attention has been given to supramolecular structures, the science of noncovalent assembly in biological systems and chemical processes [12]. Hyperbranched polymers such as polyglycerols (HPG), as a result of their inherent dendritic

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

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

Beilstein J. Org. Chem. 2012, 8, 1610–1618, doi:10.3762/bjoc.8.184

• number of works that showed their use as solvents or as solvents for synthesis and catalysis [4][5][6]. In this context ILs, which have polar and nonpolar regions, could play an important role in the field of supramolecular organization of different supramolecular structures (such as polyrotaxanes or

Chiral recognition of ephedrine: Hydrophilic polymers bearing β-cyclodextrin moieties as chiral sensitive host molecules

• Sabrina Gingter and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 1516–1519, doi:10.3762/bjoc.7.177

• -containing polymer. The supramolecular structures obtained by complexation of ephedrine and cyclodextrin were verified by 2-D ROESY NMR measurements. Dynamic light scattering showed clear differences in the mean coil size. Keywords: chiral recognition; cyclodextrins; ephedrine; host–guest interaction

• recognition with a CD-containing polymer complexed with (+)- or (−)-ephedrine. The supramolecular structures obtained by complexation of ephedrine and CD were detected by 2-D ROESY NMR measurements. Dynamic light scattering exhibited clear differences of 5 nm in the mean coil size, between the two enantiomers

• ) and the supramolecular structure 2 (35 °C). DLS measurement showing hydrodynamic diameters for (a) the CD-comprising polymer and (b) for supramolecular structures with (+)-and (−)-ephedrine respectively. Synthetic pathway to the desired β-cyclodextrin-comprising copolymer and its supramolecular system.

Chiral recognition of macromolecules with cyclodextrins: pH- and thermosensitive copolymers from N-isopropylacrylamide and N-acryloyl-D/L-phenylalanine and their inclusion complexes with cyclodextrins

• Sabrina Gingter,
• Ella Bezdushna and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 204–209, doi:10.3762/bjoc.7.27

• colour as Figure 5 shows. To prove further the influence of complexation of chiral polymers 3D and 3L with chiral RAMEB-CD, we employed dynamic light scattering to measure particle size and hydrodynamic diameters of the supramolecular structures (Figure 6). Evidently, the 3D and 3L copolymers possess

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• reversible cis/trans-isomerization provides an additional pathway for rearranging the supramolecular structures and achieving ordered supramolecular structures to produce well-dispersed nanofibers as the matrices of the hydrogels. The fact that compound 6 has the lowest molecular weight amongst the peptide

Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects

• Janja Makarević,
• Milan Jokić,
• Leo Frkanec,
• Vesna Čaplar,
• Nataša Šijaković Vujičić and
• Mladen Žinić

Beilstein J. Org. Chem. 2010, 6, 945–959, doi:10.3762/bjoc.6.106

• finally result in the formation of amyloid plaques [1][2][3][4]. During the last two decades there has been a growing interest in self-organization of small peptide models capable of self-assembling into highly organized supramolecular structures with potential use as novel bio- or nano-materials

Pyridinium based amphiphilic hydrogelators as potential antibacterial agents

• Sayanti Brahmachari,
• Sisir Debnath,
• Sounak Dutta and
• Prasanta Kumar Das

Beilstein J. Org. Chem. 2010, 6, 859–868, doi:10.3762/bjoc.6.101

• formation of three dimensional higher ordered structures during self-assembled hydrogelation was investigated by field emission scanning electron microscopy (FESEM). Morphology of the dried xerogels showed the formation of different supramolecular structures that are involved in the gelation process of 1

Calix[4]arene-click-cyclodextrin and supramolecular structures with watersoluble NIPAAM-copolymers bearing adamantyl units: “Rings on ring on chain”

• Bernd Garska,
• Monir Tabatabai and
• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, 784–788, doi:10.3762/bjoc.6.83

Anthracene functionalized terpyridines – synthesis and properties

• Falk Wehmeier and
• Jochen Mattay

Beilstein J. Org. Chem. 2010, 6, No. 54, doi:10.3762/bjoc.6.54

• blocks for photochromic supramolecular structures. A possible explanation for the observed irreversible photoreaction may be an unsymmetrical [4 + 4]-cycloaddition, connecting the anthracene moieties via the 1,4:9′,10′- instead of the 9,10:9′,10′-positions. The line-shape and the absorption increase for

Templated versus non-templated synthesis of benzo-21-crown-7 and the influence of substituents on its complexing properties

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2010, 6, No. 14, doi:10.3762/bjoc.6.14

• self-sorting [26][27] which ensures programmability and positional control of all distinct subunits present in the complexes. Along this line, more diverse and complex supramolecular structures could be obtained when suitable instructions are written into the structures of their components

Molecular recognition. 1. Crystal structures of hexaazamacrocyclic amines containing p-xylylene spacers and their adducts with acids

• Teresa Borowiak,
• Grzegorz Dutkiewicz,
• Maciej Kubicki,
• Marek Pietraszkiewicz,
• Agnieszka Gil and
• Rainer Mattes

Beilstein J. Org. Chem. 2005, 1, No. 16, doi:10.1186/1860-5397-1-16

• basicity, 1 can be highly protonated in acidic media and can form supramolecular assemblies with different anions. Two new supramolecular structures arise from self-assembly of the salt of 1 with fumaric acid and of the N-methyl derivative of 1. Keywords: Crystal structures; Macrocyclic amines; Fumaric

• efficiency in activation of substrates. This leads to numerous properties as magnetic, electronic or catalytic. [1][3][4][5] In our previous paper we described the supramolecular structures of 1,5,9,18,22,26-hexaaza [11.11]-p-cyclophane (hereafter 1, Scheme 1) complexes with o-nitrophenol and hydrochloric

• due to the shape of the macrocyclic component into two-dimensional sheets whose heights are the same as the height of the macrocyclic cation, i.e. 12.61 Å and no more similarity exists between the supramolecular structures of 1-FUM and of 1 with HCl, HBr, and o-nitrophenol. Within the sheet