Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

• Jan-Erik Ostwaldt,
• Christoph Hirschhäuser,
• Stefan K. Maier,
• Carsten Schmuck and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2021, 17, 105–114, doi:10.3762/bjoc.17.11

• identification of one compound as a promising VII. Keywords: noncovalent interactions; polymers; ring-chain transformation; supramolecular chemistry; viscosity; Introduction Viscosity index improvers (VIIs) are used to counteract the loss of viscosity of working fluids (such as motor oils) at elevated

The fluorescence of a mercury probe based on osthol

• Guangyan Luo,
• Zhishu Zeng,
• Lin Zhang,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2021, 17, 22–27, doi:10.3762/bjoc.17.3

• Guangyan Luo Zhishu Zeng Lin Zhang Zhu Tao Qianjun Zhang Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China 10.3762/bjoc.17.3 Abstract The ability of osthol (OST) to recognize mercury ions in aqueous solution was studied using

Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation

• Tereza Horáčková,
• Jan Budka,
• Vaclav Eigner,
• Wen-Sheng Chung,
• Petra Cuřínová and
• Pavel Lhoták

Beilstein J. Org. Chem. 2020, 16, 2999–3007, doi:10.3762/bjoc.16.249

• most important branches of modern supramolecular chemistry, as can easily be demonstrated by an immense number of recent reviews [1][2][3][4][5][6] and books [7][8][9][10][11] devoted to this topic. Due to the omnipresence of anions in biological systems, their irreplaceable roles in cell functioning

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• Attribution 3.0 Unported Licence, https://creativecommons.org/licenses/by/3.0/. Published by The Royal Society of Chemistry. Acknowledgements The author would like to thank late Prof. Dr. Carsten Schmuck for his exceptional contribution to Supramolecular Chemistry and Peptide Chemistry research.

Construction of pillar[4]arene[1]quinone–1,10-dibromodecane pseudorotaxanes in solution and in the solid state

• Xinru Sheng,
• Errui Li and
• Feihe Huang

Beilstein J. Org. Chem. 2020, 16, 2954–2959, doi:10.3762/bjoc.16.245

• the further capping of the pseudorotaxanes to construct rotaxanes. Keywords: host–guest chemistry; pillar[4]arene[1]quinones; pillararenes; pseudorotaxanes; supramolecular chemistry; Introduction Relying on the research of basic science, supramolecular chemistry has become an important mean for

• architectures and chemical topology [12][13][14][15][16][17][18][19][20][21][22][23]. Seeking new systems to produce pseudorotaxanes is currently considered a “hot topic” in supramolecular chemistry. As a new class of supramolecular macrocyclic hosts, pillararenes have received extensive attention in recent

UV resonance Raman spectroscopy of the supramolecular ligand guanidiniocarbonyl indole (GCI) with 244 nm laser excitation

• Tim Holtum,
• Vikas Kumar,
• Daniel Sebena,
• Jens Voskuhl and
• Sebastian Schlücker

Beilstein J. Org. Chem. 2020, 16, 2911–2919, doi:10.3762/bjoc.16.240

• . Acknowledgements J.V. would like to thank Sarah Lampe for her contribution in development of the synthesis route for the GCI ethyl amide. Funding This work is funded by the German Research Foundation (Collaborative Research Centre CRC 1093 ‘‘Supramolecular Chemistry on Proteins’’, projects A1, A9 and A10).

Using multiple self-sorting for switching functions in discrete multicomponent systems

• Amit Ghosh and
• Michael Schmittel

Beilstein J. Org. Chem. 2020, 16, 2831–2853, doi:10.3762/bjoc.16.233

• Amit Ghosh Michael Schmittel Center of Micro and Nanochemistry and Engineering, Organische Chemie I, Universität Siegen, Adolf-Reichwein-Str. 2, D-57068 Siegen, Germany 10.3762/bjoc.16.233 Abstract Over years self-sorting has developed into a powerful tool in supramolecular chemistry, for

A heterobimetallic tetrahedron from a linear platinum(II)-bis(acetylide) metalloligand

• Matthias Hardy,
• Marianne Engeser and
• Arne Lützen

Beilstein J. Org. Chem. 2020, 16, 2701–2708, doi:10.3762/bjoc.16.220

• complexes; pyridylimine ligands; self-assembly; supramolecular chemistry; Introduction The understanding of the general design principles for the self-assembly of metallosupramolecular aggregates [1][2][3][4][5] allowed to access more and more complex and large assemblies over the past decades like

Thermodynamic and electrochemical study of tailor-made crown ethers for redox-switchable (pseudo)rotaxanes

• Henrik Hupatz,
• Marius Gaedke,
• Hendrik V. Schröder,
• Julia Beerhues,
• Arto Valkonen,
• Fabian Klautzsch,
• Sebastian Müller,
• Felix Witte,
• Kari Rissanen,
• Biprajit Sarkar and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2020, 16, 2576–2588, doi:10.3762/bjoc.16.209

• Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany Department of Chemistry, University of Jyvaskyla P. O. Box 35, 40014 Jyväskylä, Finland 10.3762/bjoc.16.209 Abstract Crown ethers are common building blocks in supramolecular chemistry and are frequently applied as cation sensors or as subunits in

• ; redox chemistry; rotaxanes; supramolecular chemistry; Introduction Pedersen discovered crown ethers in 1967 while searching for multidentate ligands for the vanadyl group [1][2][3]. He was later awarded the Nobel Prize in Chemistry for his studies on the crown ether selective binding properties towards

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• : fullerenes; host–guest systems; microspheres; supramolecular chemistry; tribenzotriquinacene; Introduction In the field of supramolecular chemistry, host–guest association through noncovalent interactions is an interesting and exciting topic, especially for the encapsulation of various fullerenes, such as

NMR Spectroscopy of supramolecular chemistry on protein surfaces

• Peter Bayer,
• Anja Matena and
• Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

• interaction of proteins with their interaction partners, both biomolecules and synthetic ligands. In recent years, the focus in chemistry has kept expanding from targeting small binding pockets in proteins to recognizing patches on protein surfaces, mostly via supramolecular chemistry, with the goal to

• modulate protein–protein interactions. Here we present NMR methods that have been applied to characterize these molecular interactions and discuss the challenges of this endeavor. Keywords: molecular recognition; NMR; protein ligand interaction; protein surfaces; supramolecular chemistry; Introduction In

• as distance of targeted residues and their dynamics - must be taken into account. Supramolecular chemistry is ideally suited to address these challenges because it merges the knowledge of non-covalent molecular recognition with the possibility to combine multiple recognition units into one molecule

Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

• David Van Craen,
• Jenny Begall,
• Johannes Großkurth,
• Leonard Himmel,
• Oliver Linnenberg,
• Elisabeth Isaak and
• Markus Albrecht

Beilstein J. Org. Chem. 2020, 16, 2338–2345, doi:10.3762/bjoc.16.195

• providing the stereoinformation necessary for induction during the C–C bond formation. Catalytic approaches for C–C bond-forming reactions even found their way into the relatively young field of supramolecular chemistry, e.g., regioselective Diels–Alder reactions within supramolecular hosts as described by

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• Zhishu Zeng Jun Xie Guangyan Luo Zhu Tao Qianjun Zhang Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, No. 2708, South Section of Huaxi Avenue, Huaxi, Guiyang 550025, China 10.3762/bjoc.16.194 Abstract In this study, we investigated the host

Synthetic approaches to bowl-shaped π-conjugated sumanene and its congeners

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2020, 16, 2212–2259, doi:10.3762/bjoc.16.186

• generation of versatile functional organic materials. On the basis of this concept, in recent years, a handful of appealing molecules and materials have been synthesized and due to which nanotechnology as well as supramolecular chemistry are continuously attracting the recent attention of researchers

Models of necessity

• Timothy Clark and
• Martin G. Hicks

Beilstein J. Org. Chem. 2020, 16, 1649–1661, doi:10.3762/bjoc.16.137

• representations, is non-redundant in order to avoid dependencies within the ML process. These requirements are imposed by external conditions and likely future applications. Requirement (1), for instance, must in future include supramolecular chemistry, which means that the models should be able to reproduce

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

• Margareta Sohora,
• Leo Mandić and
• Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

• achieved by use of supramolecular chemistry [36][37]. For example, stereoselectivity has been reported for photochemical reactions taking place in the inclusion complexes with CD [38][39][40][41] or structurally modified CDs [42][43][44][45][46][47]. Since β-CD is often used in pharmaceutical applications

Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin

• Anna R. Bockman and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2020, 16, 509–514, doi:10.3762/bjoc.16.46

• attractive scaffold in the field of supramolecular chemistry, due to their well-defined donor/acceptor hydrogen-bonding arrays [10][11]. One limitation often encountered with the synthesis of structurally diverse pterins is the notorious insolubility in most solvents. This can be dealt with by preemptive

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• ], diiodoacetylene [15] and iodo/bromoethynyl moieties [16] have revealed that the XB-donors interacting with XB-acceptors (a nucleophilic region) are in approximately linear orientation. Besides, linearity, tunability and hydrophobicity (features of the XB ) are widely applied in crystal engineering, supramolecular

• chemistry, anion recognition, organocatalysis, materials science and tuning of biomolecular systems [17][18][19][20][21][22][23][24][25][26][27]. 1,2,3-Triazole-based XB-donors, such as 5-iodo-1,2,3-triazoles A [28][29][30][31][32][33] and 5-iodo-1,2,3-triazolium B [34][35][36][37] (Figure 1), are promising

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• Xiaodong Zhang Jun Xie Zhiling Xu Zhu Tao Qianjun Zhang Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China 10.3762/bjoc.16.9 Abstract The host–guest interactions between baicalein (BALE) and cucurbit[8]uril (Q[8]) and the

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

• Constantin Stuckhardt,
• Diederik Roke,
• Wojciech Danowski,
• Edwin Otten,
• Sander J. Wezenberg and
• Ben L. Feringa

Beilstein J. Org. Chem. 2019, 15, 2767–2773, doi:10.3762/bjoc.15.268

• rotation upon irradiation with light [38][39][40]. Moreover, they can be used as chiroptical multistate switches to control various functions in areas such as catalysis [41][42][43], soft materials [43][44][45] and supramolecular chemistry [46][47]. Employing molecular motors as ligands in SCCs provides an

A combinatorial approach to improving the performance of azoarene photoswitches

• Joaquin Calbo,
• Aditya R. Thawani,
• Rosina S. L. Gibson,
• Andrew J. P. White and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

• including imaging applications [20], photopharmacology [21], supramolecular chemistry [22][23], responsive foams [24], coordination chemistry [25] and DNA nanotechnology [26][27]. Whilst the azopyrazoles have excellent properties for use in a variety of photo-addressable applications, it remains frustrating

• -fluoroazopyrazole as part of their study of the supramolecular chemistry of these systems. Irradiating their compound at 365 nm enables near quantitative E→Z conversion, however, the 520 nm PSS provides 55% of the E-isomer. In water, this compound possesses a thermal half-life of >11 days. Herein, we present

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• of conjugated diynes (DYCM) is promoted by the benzylidyne tungsten complex II with silanolate ligands (X = OSi(Ot-Bu)3) [21][22]; this catalyst is also active in classical alkyne metathesis [23]. Complex III with chelating phenoxide ligands [24][25][26][27] is mostly applied in supramolecular

• chemistry [28][29][30][31][32], used for instance in the preparation of aryleneethynylene macrocycles and cages through alkyne metathesis [33][34][35][36][37][38][39]. Additionally, already since the 1980s the influence of fluorinated and unfluorinated alkoxide ligands has been widely investigated [40][41

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• vital importance to understand the supramolecular chemistry of pyridinearenes. Interestingly, ternary complexes of 12 containing both cation and solvent are not observed in either of the ESI-MS modes, even though in earlier studies such complexes were observed with solvent and anion [11]. This points to

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• macrocycles and focus on their application in different areas of supramolecular chemistry. The synthesis is mostly relying on the well-known “click reaction” (CuAAC) leading to 1,4-disubstituted 1,2,3-triazoles that then can be quaternized. Applications of triazolium macrocycles thus prepared include

• -triazolium macrocycles; Review 1. Introduction Supramolecular chemistry – “The chemistry beyond the molecule” [1] – is an ever growing interdisciplinary area has emerged from the early host–guest chemistry to more elaborate bio-inspired supramolecular aggregates by exploiting various noncovalent

• critical role of negatively charged species in numerous biological, environmental, chemical and medicinal processes, anion receptors and transporters play an important role in supramolecular chemistry [17][29]. Thus, diverse anion receptors based on 1,2,3-triazolium recognition elements have been reported

Multiple threading of a triple-calix[6]arene host

• Veronica Iuliano,
• Roberta Ciao,
• Emanuele Vignola,
• Carmen Talotta,
• Patrizia Iannece,
• Margherita De Rosa,
• Annunziata Soriente,
• Carmine Gaeta and
• Placido Neri

Beilstein J. Org. Chem. 2019, 15, 2092–2104, doi:10.3762/bjoc.15.207

• Veronica Iuliano Roberta Ciao Emanuele Vignola Carmen Talotta Patrizia Iannece Margherita De Rosa Annunziata Soriente Carmine Gaeta Placido Neri Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia " A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, 84084

• stereoselective formation of endo-alkyl pseudo[n]rotaxane stereoisomers. Keywords: calixarene; multiple-threading; pseudo[n]rotaxane; stereoisomers; Introduction The self-assembly [1] of smaller components to larger aggregates represents one of the most spectacular phenomena in supramolecular chemistry [2][3][4