Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• are cases characterized by the active participation of the surface in accelerating the self-assembly. To discriminate the processes taking place on the surface from similar processes in liquid volume, measurements were carried out immediately after the deprotonation of oligoglycine salts at incubation

Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C₆₀

• Marco Caricato,
• Silvia Díez González,
• Idoia Arandia Ariño and
• Dario Pasini

Beilstein J. Org. Chem. 2014, 10, 1308–1316, doi:10.3762/bjoc.10.132

• traditionally sought after for enhancing the recognition toward suitable guests [5][6][7][8][9][10], and for the self-assembly, of stable organic nanotubes from the macrocyclic structures as molecular building blocks [11]. Cyclic peptides [12][13][14], phenylacetylene macrocycles [15], amide-containing

• protocol for the preparation of several chiral macrocycles incorporating BINOL (1,1′-bi-2-naphthol) units, through the formation of bridging ester functionalities, which ensure chemical inertness for the purposes of supramolecular sensing, recognition, or self-assembly. We have shown their application in

A new building block for DNA network formation by self-assembly and polymerase chain reaction

• Holger Bußkamp,
• Sascha Keller,
• Marta Robotta,
• Malte Drescher and
• Andreas Marx

Beilstein J. Org. Chem. 2014, 10, 1037–1046, doi:10.3762/bjoc.10.104

• Holger Busskamp Sascha Keller Marta Robotta Malte Drescher Andreas Marx Department of Chemistry and Konstanz Research School Chemical Biology, University of Konstanz, Universitätsstraße 10, 78457 Konstanz, Germany 10.3762/bjoc.10.104 Abstract The predictability of DNA self-assembly is exploited

• in many nanotechnological approaches. Inspired by naturally existing self-assembled DNA architectures, branched DNA has been developed that allows self-assembly to predesigned architectures with dimensions on the nanometer scale. DNA is an attractive material for generation of nanostructures due to a

• plethora of enzymes which modify DNA with high accuracy, providing a toolbox for many different manipulations to construct nanometer scaled objects. We present a straightforward synthesis of a rigid DNA branching building block successfully used for the generation of DNA networks by self-assembly and

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• interactions in living systems [3][4]. Since then, the field of self-assembly through molecular recognition has attracted much attention also in the design of smart materials. In this context, cyclodextrins (CD) are of interest as ring shaped host molecules, e.g., for the design of stimuli-responsive hydrogels

Self-assembly of metallosupramolecular rhombi from chiral concave 9,9’-spirobifluorene-derived bis(pyridine) ligands

• Rainer Hovorka,
• Sophie Hytteballe,
• Torsten Piehler,
• Georg Meyer-Eppler,
• Filip Topić,
• Kari Rissanen,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 432–441, doi:10.3762/bjoc.10.40

• -protected [(dppp)Pd]2+ and [(dppp)Pt]2+ ions. The self-assembly process of the racemic ligand preferably occurs in a narcissistic self-recognising manner. Hence, a mixture of all three possible stereoisomers [(dppp)2M2{(R)-L}2](OTf)4, [(dppp)2M2{(S)-L}2](OTf)4, and [(dppp)2M2{(R)-L}{(S)-L}](OTf)4 was

• . Keywords: concave templates; metal complexes; self-assembly; self-sorting; 9,9’-spirobifluorene; supramolecular chemistry; Introduction Concave templates are versatile tools to achieve self-sorting behaviour in the self-assembly of defined aggregates from multicomponent mixtures in a social self

• -recognising [4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] or a self-discriminating manner [19][20][21][22][23][24][25][26][27]. As part of our ongoing programme to develop general guidelines for the diastereoselective self-assembly of metallosupramolecular aggregates, we have recently started a

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

• Phei Li Lau,
• Ray W. K. Allen and
• Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

• these cross-coupling methods has undoubtedly revolutionalised the protocols for the construction of natural products, building blocks for supramolecular chemistry, self-assembly of organic materials and polymers, and lead compounds in medicinal chemistry from simpler entities [1]. These include the

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• properties. UV–vis, fluorescence, mass spectrometric as well as variable-temperature 1H NMR experiments on these gels suggest that the CT interaction is one of the major driving forces for the formation of these organogels. Keywords: charge transfer; glycyrrhetinic acid; organogel; self-assembly

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

• .9.213 Abstract Supramolecular gels are an important and interesting class of soft materials that show great potential for many applications. Most of them have been discovered serendipitously, and understanding the supramolecular self-assembly that leads to the formation of the gel superstructure is the

• model of self-assembly through multiple intermolecular hydrogen bonds between the 1,2-dihydroxy system, which is based on experimental data and computational simulations revealing the importance of the di-axial orientation of the hydroxy groups for the one-dimensional self-assembly. Under controlled

• between the anionic silicate intermediate species and the self-assembled fibrillar network. Keywords: Hansen parameters; nanotube; organogel; self-assembly; supramolecular gel; Introduction Low molecular mass organogelators (LMOGs) have received increasing attention during the last two decades because

Structures of the reaction products of the AZADO radical with TCNQF₄ or thiourea

• Hideto Suzuki,
• Yuta Kawahara,
• Hiroki Akutsu,
• Jun-ichi Yamada and
• Shin’ichi Nakatsuji

Beilstein J. Org. Chem. 2013, 9, 1487–1491, doi:10.3762/bjoc.9.169

• impressively some TEMPO derivatives with appropriate acceptor units such as 1,4-benzoquinone [7] or naphthalenediimide [8] can form single-component CT complexes by self-assembly. Based on previous results, we next intended to see if similar CT complexes would be formed from AZADO (2) with an appropriate

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

• . Evidence is presented that the ability of these molecules to form one-dimensional hydrogen-bonded chains and subsequently exhibit hierarchical self-assembly into nanostructured domains can be correlated with improved device efficiency. Keywords: hydrogen-bonding; organic photovoltaics; self-assembly

• masks a known self-complementary hydrogen-bonding domain. The self-assembly properties of this unit have been extensively studied in a variety of systems [21][22][23][24][25][26], but this approach has not yet been applied to improving organic photovoltaic device performance. Solubility could be

• analysis, was reported to be at least 60 KJ mol−1 [29]. Self-assembly of cyanopyridone 2 The hydrogen-bond-mediated self-assembly behaviour of compound 2 was monitored by 1H NMR spectroscopy. The chemical shift of the proton on nitrogen in chloroform was observed to shift downfield in a concentration

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• -delivery; hydrogel; multifunctional; nanofibers; NSAID; self-assembly; supramolecular; topical use; Introduction This article reports the design, synthesis, and characterization of hydrogelators made of non-steroidal anti-inflammatory drugs (NSAID) and small peptides for the development of multifunctional

• acetylsalicylic acid (aspirin) to connect with dipeptides results in a compound hydrolyzing easily at the ester bond of aspirin, we use salicylic acid (Sal) instead to conjugate with diphenylalanine and dialanine (AA) to make compounds 5a and 5g, respectively. Self-assembly and hydrogelation After the synthesis

• diastereomer of 1a, hydrogelator 1b exhibits quite different behavior in terms of self-assembly and hydrogelation. For example, at a concentration of 0.8 wt %, 1b forms a solution at pH 9.0 and 60 °C, and the solution remains after the conditions have been adjusted to pH 7.0 and room temperature. Further

Spin state switching in iron coordination compounds

• Philipp Gütlich,
• Ana B. Gaspar and
• Yann Garcia

Beilstein J. Org. Chem. 2013, 9, 342–391, doi:10.3762/bjoc.9.39

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

• chains of proteins [6], to size control of the electrostatic self assembly of nanoparticles [7]. Also a pH-controlled release of many cyclodextrins in long stacks on polymers, such as polyrotaxanes, combined with mesoporous silica particles was observed [8]. Complex formation with solvent molecules can

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 and
• Rubén D. Sinisterra

Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215

• , suggesting that βCD is able to minimize the ferrite coalescence process in aqueous solution. The ferrite aggregation process may occur in low zeta potential values (−10 mV, see zeta potential data) and is insufficient to avoid van der Waals attraction [30]; however, at pH 7 this self-assembly behavior can

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

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175

• functionalized by self-assembly [27]. To this end, cyclodextrins are modified with long alkyl chains (“tails”) and short oligo(ethylene glycol) head groups. These macrocyclic amphiphiles form unilamellar bilayer vesicles in aqueous solution upon hydration of a thin film cast by evaporation from organic solution

• consequence, the density of mannose molecules on the surface of the vesicles is expected to be relatively high, resulting in the formation of an artificial glycocalyx by self-assembly. Therefore, the addition of the lectin ConA should lead to agglutination of the vesicles due to the specific interaction of

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

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

Beilstein J. Org. Chem. 2012, 8, 1479–1484, doi:10.3762/bjoc.8.167

• complexes and aggregates was a consequence of the competitive equilibria of CD/phosphane complexation and phosphane self-assembly to form micelles. The surface activity of the four studied phosphanes has already been the subject of investigations [7][8]. Phosphanes 1–4 proved to be very surface active as

Cyanoethylation of the glucans dextran and pullulan: Substitution pattern and formation of nanostructures and entrapment of magnetic nanoparticles

• Kathrin Fiege,
• Heinrich Lünsdorf,
• Sevil Atarijabarzadeh and
• Petra Mischnick

Beilstein J. Org. Chem. 2012, 8, 551–566, doi:10.3762/bjoc.8.63

• -forming qualities of cyanoethylpullulan [10]. Partial hydrophobization of polysaccharides by the introduction of nonpolar residues enables nanostructuring by self-assembly of these compounds. Heinze et al. demonstrated that hydrophobic dextran derivatives form spherical particles on the nanometer scale

Liquid-crystalline nanoparticles: Hybrid design and mesophase structures

• Gareth L. Nealon,
• Romain Greget,
• Cristina Dominguez,
• Zsuzsanna T. Nagy,
• Daniel Guillon,
• Jean-Louis Gallani and
• Bertrand Donnio

Beilstein J. Org. Chem. 2012, 8, 349–370, doi:10.3762/bjoc.8.39

• morphology (size, shape and roughness) and can be manipulated by coating with suitable structure-directing agents. Amongst the techniques used to assemble NPs, self-assembly methods show immense promise towards achieving the ambitious results expected from the field of nanotechnology research [23]. Liquid

• observed. Columnar ordering of pseudospherical cores functionalised with laterally substituted mesogens has been observed previously for liquid-crystalline silsesquioxanes [72][73][74], indicating that this self-assembly motif may prove to be quite general. Importantly, this work demonstrated that the

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• Sankarasekaran Shanmugaraju Dipak Samanta Partha Sarathi Mukherjee Department of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore-560 012, India. Fax: 91-80-2360-1552; Tel: 91-80-2293-3352 10.3762/bjoc.8.34 Abstract Coordination-driven self-assembly of binuclear half

• tetranuclear rectangular geometry with the dimensions of 5.53 Å × 12.39 Å. Furthermore, the photo- and electrochemical properties of these newly synthesized assemblies have been studied by using UV–vis absorption and cyclic voltammetry analysis. Keywords: cages; macrocycles; ruthenium(II); self-assembly; self

• -sorting; Introduction Self-assembly of metal-based molecular architectures through coordination has emerged as an active field of research as large numbers of intricate structural motifs can easily be derived in a single step from predesigned molecular building units. In the last two decades several

Synthesis of multivalent host and guest molecules for the construction of multithreaded diamide pseudorotaxanes

• Nora L. Löw,
• Egor V. Dzyuba,
• Boris Brusilowskij,
• Lena Kaufmann,
• Elisa Franzmann,
• Wolfgang Maison,
• Emily Brandt,
• Daniel Aicher,
• Arno Wiehe and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2012, 8, 234–245, doi:10.3762/bjoc.8.24

• these concepts are not only molecular recognition and the noncovalent bonds themselves, but also self-assembly, self-sorting, templation and multivalent binding [1][2][3][4][5][6][7][8]. Consequently, the reductionist investigation of synthetic supramolecules can help us to understand biological systems

Computational evidence for intramolecular hydrogen bonding and nonbonding X···O interactions in 2'-haloflavonols

• Tânia A. O. Fonseca,
• Matheus P. Freitas,
• Rodrigo A. Cormanich,
• Teodorico C. Ramalho,
• Cláudio F. Tormena and
• Roberto Rittner

Beilstein J. Org. Chem. 2012, 8, 112–117, doi:10.3762/bjoc.8.12

• interactions; theoretical calculations; Introduction Intermolecular hydrogen bonding (HB) is an interaction governing self-assembly and is responsible for the architecture and organization of molecular aggregates [1], and also ligand–receptor interactions that are responsible for the bioactivity of compounds

Impact of the level of complexity in self-sorting: Fabrication of a supramolecular scalene triangle

• Kingsuk Mahata and
• Michael Schmittel

Beilstein J. Org. Chem. 2011, 7, 1555–1561, doi:10.3762/bjoc.7.183

• various scalene triangles. It turned out that the self-sorting system with a higher level of complexity was far superior to less complex sorting algorithms. Keywords: copper; metallosupramolecular chemistry; phenanthroline; self-assembly; self-sorting; Introduction Self-assembly guided by self-sorting

• attributed to [Cu2Zn(5)(6)(7)](OTf)3+, and the doubly charged one at m/z = 1481.1 to [Cu2Zn(5)(6)(7)](OTf)22+. All peaks were isotopically resolved, showing full agreement with the theoretically expected isotopic distribution. To corroborate the clean self-assembly process, we carefully examined the DOSY and

• the 1H NMR (Figure 3b), but the many signals in the region 2.5–4.0 ppm suggest formation of several species. Thus, a comparison among the NMR spectra nicely demonstrated that the self-assembly process was only clean in the case of the mixed-metal scenario, whereas the situation turned out to be

Supramolecular chemistry II

• Christoph A. Schalley

Beilstein J. Org. Chem. 2011, 7, 1541–1542, doi:10.3762/bjoc.7.181

• sciences on the other. In the life sciences, the networks of noncovalent interactions between the constituents of cells, for example, have shifted into the current focus. Self-assembly, templation, self-sorting and multivalent binding all contribute to setting up the extremely complex architecture of a

Protonation and deprotonation induced organo/hydrogelation: Bile acid derived gelators containing a basic side chain

• Uday Maitra and
• Arkajyoti Chakrabarty

Beilstein J. Org. Chem. 2011, 7, 304–309, doi:10.3762/bjoc.7.40

• properties, such as stimuli sensitivity. Their self-assembly in nanoscale superstructures are likely to have important implications in accessing functional nanomaterials [1]. The types of superstructures generated by the SAFINs (Self-Assembled Fibrillar Networks) include fibres, rods, and ribbons. Such self

Synthesis and self-assembly of 1-deoxyglucose derivatives as low molecular weight organogelators

• Guijun Wang,
• Hao Yang,
• Sherwin Cheuk and
• Sherman Coleman

Beilstein J. Org. Chem. 2011, 7, 234–242, doi:10.3762/bjoc.7.31

• sugar headgroup towards self-assembly, we synthesized a series of 1-deoxyglucose analogs, and examined their gelation properties in several solvents. Several long chain esters, including diacetylene containing esters, and aryl esters exhibited gelation in ethanol, aqueous ethanol, or aqueous DMSO. The

• synthesis and characterization of these novel analogs are reported. Keywords: 1,5-anhydroglucitol; carbohydrate; hydrogelator; organogelator; self-assembly; Introduction In recent years, the field of low molecular weight gelators (LMWGs) has received a great deal of attention. LMWGs are an interesting

• class of small molecules that can form reversible supramolecular gels in organic solvents or aqueous solutions [1][2][3][4][5][6][7][8][9]. Non-covalent interactions such as hydrogen bonding, hydrophobic interactions, and π–π stacking are the main driving forces for the self-assembly of the gelators