Substitution effect and effect of axle’s flexibility at (pseudo-)rotaxanes

• Friedrich Malberg,
• Jan Gerit Brandenburg,
• Werner Reckien,
• Oldamur Hollóczki,
• Stefan Grimme and
• Barbara Kirchner

Beilstein J. Org. Chem. 2014, 10, 1299–1307, doi:10.3762/bjoc.10.131

• binding is weakened by approximately 10 kcal/mol, and hydrogen bonds are slightly shortened (by up to 0.2 Å). Keywords: dispersion interaction; hydrogen bond; supramolecular chemistry; template; theoretical chemistry; Introduction Rotaxanes are prototypes for molecular machines and molecular switches [1

The influence of intraannular templates on the liquid crystallinity of shape-persistent macrocycles

• Joscha Vollmeyer,
• Ute Baumeister and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 910–920, doi:10.3762/bjoc.10.89

• planar. Keywords: discotic liquid crystals; shape-persistent macrocycles; templates; X-ray scattering; Introduction The supramolecular chemistry of shape-persistent macrocycles has enormously expanded during the past several years [1][2][3][4][5][6]. It covers the non-covalent interaction between the

Molecular recognition of isomeric protonated amino acid esters monitored by ESI-mass spectrometry

• Andrea Liesenfeld and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 825–831, doi:10.3762/bjoc.10.78

• . However, mass spectrometry has become a major analytical tool in supramolecular chemistry in recent years [19][20][21] and seemed to be perfectly suited in this case, since we were planning to recognise the amino acid derivatives in form of their protonated alkyl esters anyway. Thus, the host–guest

Towards allosteric receptors – synthesis of β-cyclodextrin-functionalised 2,2’-bipyridines and their metal complexes

• Christopher Kremer,
• Gregor Schnakenburg and
• Arne Lützen

Beilstein J. Org. Chem. 2014, 10, 814–824, doi:10.3762/bjoc.10.77

• bringing together or separating the cyclodextrin moieties from each other. Keywords: allosteric receptors; 2,2’-bipyridines; β-cyclodextrin; supramolecular chemistry; metal complexes; Introduction In biological systems, recognition events play a major role to guarantee the selectivity of essential

• ) or hampering (negative allosteric cooperativity) the binding of another substrate at a second binding site. This powerful regulatory concept has become quite interesting in supramolecular chemistry, and the development of artificial receptor systems which can be controlled by allosteric effects comes

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

• functionalization is supported by 1H NMR-, SEC-, FTIR- and MALDI–TOF measurements. Keywords: chain-transfer polymerization; cyclodextrins; end-group functionalization; host–guest interaction; lower critical solution temperature (LCST); poly(N,N-diethylacrylamide); Introduction Supramolecular chemistry was first

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

• . 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

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

• ; Introduction The creation of one-dimensional (1D) nanostructures is one of the focused fields in supramolecular chemistry [1][2][3][4]. In order to control the molecular arrangement in 1D structures, low molecular weight gelators (LMWGs) have generated considerable interest during the past decade [5][6]. The

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

• particular as templates for tracing air-borne arenes at low concentration. The affinities of the synthesized materials towards different air-borne arenes were determined by 200 MHz quartz crystal microbalances. Keywords: affinity materials; (−)-Isosteviol; supramolecular chemistry; triphenylene ketals

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• geometric features of its skeleton with a D3h symmetry have attracted a lot of attention and its derivatives have been used for applications in supramolecular chemistry, material chemistry, and as molecular machines [1][2]. The interest in this three-dimensional rigid platform is also due to the easy

Structure elucidation of β-cyclodextrin–xylazine complex by a combination of quantitative ¹H–¹H ROESY and molecular dynamics studies

• Syed Mashhood Ali,
• Kehkeshan Fatma and
• Snehal Dhokale

Beilstein J. Org. Chem. 2013, 9, 1917–1924, doi:10.3762/bjoc.9.226

• ; Introduction The emergence and establishment of supramolecular chemistry as an important domain of science has fueled the development of complex chemical systems from components, interacting by non-covalent intermolecular forces. This field transcends the traditional barriers separating many disciplines of

• science and is the basis for most of the vital biological processes [1]. The basis of supramolecular chemistry is molecular recognition where host and guest species interact with each other and exist as a single system. These host–guest systems symbolize simplest examples of supramolecular systems in

Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production

• Sándor B. Ötvös,
• Ádám Georgiádes,
• István M. Mándity,
• Lóránd Kiss and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172

• applications in numerous other areas of modern chemical sciences, such as bioconjugation [13], supramolecular chemistry, [14] and polymer sciences [15]. Probably the most useful and powerful procedure for the synthesis of 1,2,3-triazoles is the Huisgen 1,3-dipolar cycloaddition of organic azides with

Isolation and X-ray characterization of palladium–N complexes in the guanylation of aromatic amines. Mechanistic implications

• Abdessamad Grirrane,
• Hermenegildo Garcia and
• Eleuterio Álvarez

Beilstein J. Org. Chem. 2013, 9, 1455–1462, doi:10.3762/bjoc.9.165

• catalysis; palladium complexes; reactive intermediates; Introduction N-Arylguanidines are important compounds with interesting biological activities [1][2] such as fungicides [3] and also in supramolecular chemistry as complementary partners of carboxylate and nitro groups [4][5][6][7]. Some of these

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

• verified by the shifts of the protons in the 1H NMR spectra and in the correlation signals of the 2D ROESY NMR spectra. Keywords: cyclodextrins; ferrocene; host–guest systems; polysiloxanes; supramolecular chemistry; Introduction Polymers containing cyclodextrins (CD) covalently or supramolecularly

Host–guest complexes of mixed glycol-bipyridine cryptands: prediction of ion selectivity by quantum chemical calculations, part V

• Svetlana Begel,
• Ralph Puchta and
• Rudi van Eldik

Beilstein J. Org. Chem. 2013, 9, 1252–1268, doi:10.3762/bjoc.9.142

• -inorganic supramolecular chemistry, which requires detailed and elaborate examination due to its significant role in receptors in biological and technical systems. Selectivity phenomena have been studied for over 80 years [5][6]. During this period of time versatile model systems with variable cavity sizes

Efficient electroorganic synthesis of 2,3,6,7,10,11-hexahydroxytriphenylene derivatives

• Carolin Regenbrecht and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2012, 8, 1721–1724, doi:10.3762/bjoc.8.196

• common structural motif. The use of triphenylenes in discotic liquid crystals [1][2] as building blocks in supramolecular chemistry [3][4] as well as in solid-state chemistry [5] is well documented. Furthermore, triphenylenes are applied as components of functional polymers [6][7] and fluorescent labels

Synthesis and anion recognition properties of shape-persistent binaphthyl-containing chiral macrocyclic amides

• Marco Caricato,
• Nerea Jordana Leza,
• Claudia Gargiulli,
• Giuseppe Gattuso,
• Daniele Dondi and
• Dario Pasini

Beilstein J. Org. Chem. 2012, 8, 967–976, doi:10.3762/bjoc.8.109

• electronic features of the functional groups in the 2,2' positions. Keywords: amides; anion recognition; chirality; macrocycles; molecular switches; supramolecular chemistry; Introduction Macrocyclic molecules possessing a high degree of shape persistency act as molecular cages, and the scientific interest

Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions

• Yagang Zhang and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2012, 8, 486–495, doi:10.3762/bjoc.8.55

• -diamido-1,8-naphthyridine (DAN); polymer; quadruply hydrogen bonding; supramolecular; Introduction Lehn’s pioneering studies [1] have advanced supramolecular chemistry to the point where complex hierarchical self-assembled [2] and even dynamically assembled structures are routinely described [3

Synthesis of mesomeric betaine compounds with imidazolium-enolate structure

• Nina Gonsior,
• Fabian Mohr and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 390–397, doi:10.3762/bjoc.8.42

• ). Regarding our interest in supramolecular chemistry and the enhancement of water solubility, the ability of 3 to form inclusion complexes with randomly methylated (1.8) β-cyclodextrin (m-β-CD) was investigated by means of UV–vis spectroscopy. Therefore, the type of inclusion complex and the complex formation

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

• wheel precursors. Keywords: multivalency; pseudorotaxanes; Sonogashira coupling; supramolecular chemistry; tetralactam macrocycles; Introduction Synthetic supramolecular complexes have the great potential to put those concepts to the test that govern much of the noncovalent chemistry in nature. Among

Fifty years of oxacalix[3]arenes: A review

• Kevin Cottet,
• Paula M. Marcos and
• Peter J. Cragg

Beilstein J. Org. Chem. 2012, 8, 201–226, doi:10.3762/bjoc.8.22

• supramolecular chemistry, are 2,6-metacyclophanes with a methylene bridge between their phenolic groups, as shown in Figure 1 [1][2][3]. In 1994, the term “homocalixarene” was coined by Brodesser and Vögtle to describe analogues of calixarenes with two or more methylene groups between the aromatic moieties [4

Thermodynamic and kinetic stabilization of divanadate in the monovanadate/divanadate equilibrium using a Zn-cyclene derivative: Towards a simple ATP synthase model

• Hanno Sell,
• Anika Gehl,
• Frank D. Sönnichsen and
• Rainer Herges

Beilstein J. Org. Chem. 2012, 8, 81–89, doi:10.3762/bjoc.8.8

• thermodynamically as shown by NMR titration. Moreover, EXSY NMR experiments reveal that the vanadate dimer is also kinetically stabilized with respect to hydrolysis by complexation with Zn-cyclene. Keywords: EXSY NMR; NMR titration; supramolecular chemistry; vanadate condensation; 51V NMR; Zn-cyclene

• ; Introduction Driving endergonic reactions with external energy sources is one of the challenging and so far unsolved problems in supramolecular chemistry. The best known example in nature is probably the condensation of phosphate and ADP to ATP, driven by a proton gradient across a membrane [1]. There are a

Structural conditions required for the bridge lithiation and substitution of a basic calix[4]arene

• Conrad Fischer,
• Wilhelm Seichter and
• Edwin Weber

Beilstein J. Org. Chem. 2011, 7, 1602–1608, doi:10.3762/bjoc.7.188

• new monobridge-substituted calix[4]arenes were characterized with respect to their conformational behaviour in solution and the X-ray crystal structure of one key intermediate is taken into consideration. Keywords: calixarene; lithiation; methylene bridge; supramolecular chemistry; X-ray structure

Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

• Michael Zengerle,
• Florian Brandhuber,
• Christian Schneider,
• Franz Worek,
• Georg Reiter and
• Stefan Kubik

Beilstein J. Org. Chem. 2011, 7, 1543–1554, doi:10.3762/bjoc.7.182

• units, represent one of the most important classes of host systems in supramolecular chemistry [1]. Their easy availability, their ability to include organic nonpolar molecules into the cavity made up by the cyclically arranged glucose units in aqueous solution, their predictable and controllable

Supramolecular chemistry II

• Christoph A. Schalley

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

• Christoph A. Schalley Institut für Chemie und Biochemie - Organische Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin, Germany 10.3762/bjoc.7.181 Supramolecular chemistry is a rapidly growing field, which has had remarkable impact on the life sciences on one hand and on materials

• devoted to quantifying host–guest interactions, aiming at a more profound understanding of the subtle entropic and enthalpic effects that govern the interactions between host and guest. A first Thematic Series devoted to supramolecular chemistry was assembled about two years ago and published by the

• synthetic receptors, crystallographic studies of halogen bonding and the use of polymers for protein binding. The second series again has a broad scope, as you will discover in the coming months as the series develops. With the second Thematic Series on supramolecular chemistry, we wish to contribute to the