Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

• Aderonke Ajibola Adeyemo and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2018, 14, 2242–2249, doi:10.3762/bjoc.14.199

• [47][48][49][50][51] and host–guest chemistry [52][53][54][55][56] among others. The cardinal prerequisites to obtain these self-assembled supramolecular architectures include stoichiometry and conformational complementarity on the binding sites of the building blocks [57][58][59][60][61]. However

Coordination-driven self-assembly vs dynamic covalent chemistry: versatile methods for the synthesis of molecular metallarectangles

• Li-Li Ma,
• Jia-Qin Han,
• Wei-Guo Jia and
• Ying-Feng Han

Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

• metallarectangles, metallacages and Borromean-type rings. Moreover, many of these structures have been utilized for various applications, such as catalysts, host–guest chemistry and others [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Through the use of a range of diverse functional ligands, the

An amphiphilic pseudo[1]catenane: neutral guest-induced clouding point change

• Tomoki Ogoshi,
• Tomohiro Akutsu and
• Tada-aki Yamagishi

Beilstein J. Org. Chem. 2018, 14, 1937–1943, doi:10.3762/bjoc.14.167

• –guest chemistry [5][6][7]. The molecules consist of a non-ionic amphiphilic part containing tri(ethylene oxide) moieties, and a hydrophobic part consisting of a pillar[n]arene core (Figure 1a; 1, n = 5; 2, n = 6). Pillar[n]arenes, which were first reported by our group [11], were used as the macrocyclic

• , which exhibits a clouding point around 32 °C [1][2][3][4]. Recently, thermo-responsive molecules with additional functions have been developed to replace pNIPAAm [5][6][7][8][9][10]. For example, we have developed thermo-responsive macrocyclic molecules which exhibit LCST behavior regulated by host

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

• Rakesh Puttreddy,
• Ngong Kodiah Beyeh,
• S. Maryamdokht Taimoory,
• Daniel Meister,
• John F. Trant and
• Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

• , aiding in the binding of polar guests such as N-oxides. Keywords: aromatic N-oxides; C–H···π Interactions; ditopic receptors; endo/exo complexation; host–guest chemistry; resorcinarenes; Introduction Resorcinarenes are macrocyclic compounds with a bowl-shaped cavity stabilised by circular

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

• Liu-Pan Yang,
• Song-Bo Lu,
• Arto Valkonen,
• Fangfang Pan,
• Kari Rissanen and
• Wei Jiang

Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

• changes are rare. In this article, we present a thorough study on the host–guest chemistry of a conformationally adaptive macrocycle, namely per-O-ethoxyzorb[4]arene (ZB4). Similar to per-O-ethoxyoxatub[4]arene, ZB4 is capable of accommodating a wide range of organic cations. However, ZB4 does not show

• binding behavior of ZB4 and lays the basis for the construction of stimuli-responsive materials with ZB4 as a major component. Keywords: conformations; host–guest chemistry; macrocycles; supramolecular chemistry; zorb[4]arene; Introduction Macrocyclic receptors are the principal workhorses used in

Complexation of molecular clips containing fragments of diphenylglycoluril and benzocrown ethers with paraquat and its derivatives

• Leonid S. Kikot',
• Catherine Yu. Kulygina,
• Alexander Yu. Lyapunov,
• Svetlana V. Shishkina,
• Roman I. Zubatyuk,
• Tatiana Yu. Bogaschenko and
• Tatiana I. Kirichenko

Beilstein J. Org. Chem. 2017, 13, 2056–2067, doi:10.3762/bjoc.13.203

• size and the nature of the substituents at the nitrogen atoms of the paraquat derivatives on the composition and stability of these complexes. Keywords: complexation; crown ethers; "host–guest chemistry"; molecular clips; paraquat; Introduction After the first report on the synthesis of crown ethers

• and their complexation properties made by Pedersen in 1967, "host–guest chemistry" attracted great attention [1]. In subsequent years, various types of crown compounds have been obtained, their complexation with metal ions, ammonium, and alkylammonium salts has been extensively studied. After Stoddart

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• Loic Leclercq Univ. Lille, CNRS, ENSCL, UMR 8181 – UCCS - Equipe CÏSCO, F-59000 Lille, France 10.3762/bjoc.12.261 Abstract In the field of host–guest chemistry, some of the most widely used hosts are probably cyclodextrins (CDs). As CDs are able to increase the water solubility of numerous drugs

• ; greener active ingredients; host–guest chemistry; lipids; Introduction Cyclodextrins (CDs) were discovered and identified over a century ago [1][2][3]. Between 1911 and 1935, Pringsheim and co-workers demonstrated the ability of CDs to form complexes with many organic molecules [4][5]. Since the 1970s

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• cyclodextrin vesicle surface. The supramolecular immobilization was monitored by using fluorescence spectroscopy and microscopy and the photochemistry of the squaraine was investigated by using absorption spectroscopy. Keywords: cyclodextrin; host–guest chemistry; photodynamic therapy; self-assembly

Supramolecular chemistry at the interface of biology, materials and medicine

• Eric V. Anslyn and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 1101–1102, doi:10.3762/bjoc.12.105

• Eric V. Anslyn Steven C. Zimmerman Department of Chemistry, University of Texas, Austin, TX 78712, United States Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, United States 10.3762/bjoc.12.105 Keywords: biomimetic chemistry; host–guest chemistry

From steroids to aqueous supramolecular chemistry: an autobiographical career review

• Bruce C. Gibb

Beilstein J. Org. Chem. 2016, 12, 684–701, doi:10.3762/bjoc.12.69

• was that I had “discovered” molecular concavity and host–guest chemistry, research that I instantly related to the action of the Cytochrome P-450s and other enzymes. Unfortunately however, there was the small problem of financial support. From John’s perspective I had literally appeared out of the

A journey in bioinspired supramolecular chemistry: from molecular tweezers to small molecules that target myotonic dystrophy

• Steven C. Zimmerman

Beilstein J. Org. Chem. 2016, 12, 125–138, doi:10.3762/bjoc.12.14

• early career efforts in molecular recognition, especially molecular tweezers. Although designed to complex DNA, these hosts proved more applicable to the field of host–guest chemistry. This early experience and interest in intercalation ultimately led to the current efforts to develop small molecule

• tweezers and a paradigm shift in host–guest chemistry Developing molecular tweezers was one of the main projects I started in my independent academic career at Illinois. The idea originated at Columbia when I began to teach myself the biochemistry and biology lacking in any of my formal coursework. For

• excitement surrounding the 1987 Nobel Prize to Cram, Lehn, and Pedersen had generated an enormous interest in host–guest chemistry and there was at this time a move to go beyond cyclic crown ethers. In particular, the groups of Rebek [11] and Hamilton [12] and many others were developing hosts capable of

Supramolecular polymer assembly in aqueous solution arising from cyclodextrin host–guest complexation

• Jie Wang,
• Zhiqiang Qiu,
• Yiming Wang,
• Li Li,
• Xuhong Guo,
• Duc-Truc Pham,
• Stephen F. Lincoln and
• Robert K. Prud’homme

Beilstein J. Org. Chem. 2016, 12, 50–72, doi:10.3762/bjoc.12.7

• Cyclodextrin host–guest chemistry is characterized by an ever-expanding range of host and guests, some of which undergo structural and interaction variations in response to stimuli as exemplified by photo-, pH-, temperature- and redox-responsive changes. Consequently, cyclodextrins have generated a range of

• /adamantane carboxylate complexation prevents self-healing ((c) and (e)). The properties of this hydrogel can also be utilized in controlling expansion and contraction and shape memory. The practical applications which potentially flow at the macroscopic level from such host–guest chemistry are substantial

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• (s) between the aromatic rings and also provide flexibility to the overall structure. Cyclophanes play an important role in “host–guest” chemistry [39][40][41][42][43] and supramolecular assembly [44][45][46][47]. “Phane”-containing molecules show interactions with π-systems, and they can also bind

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• Veronique Nardello-Rataj Loic Leclercq Université de Lille, Sciences et Technologies, EA 4478, Chimie Moléculaire et Formulation, F-59655 Villeneuve d’Ascq Cedex, France 10.3762/bjoc.10.273 Abstract Host–guest chemistry is useful for the construction of nanosized objects. Some of the widely used

• : cyclodextrin; biocide; encapsulation; host–guest chemistry; pathogen; textile; Introduction Since the first reference to cyclodextrins (CDs) in 1891 by Villiers, CD has been of great interest to researchers [1]. Cyclodextrins are composed of several α-D-glucopyranose units linked 1→4 and arranged in a conical

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

• realize sequence-specific molecular recognition by the use of host–guest chemistry, but the recognition motifs as well as the linkages have to be chosen very carefully. In the case of trivalent systems one adamantane moiety must be included to induce preferred formation of 1:1 adducts. Due to the too weak

• transferred to artificial systems like peptide nucleic acids (PNA) [33] and extensively used to mimic biological processes [34][35] or to generate functional materials [36]. Host–guest chemistry has been studied in the field of sequence-specific molecular recognition as well. The selective recognition of

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

• tool to study the host–guest chemistry of these systems in the future, however, we did not investigate these further. Interestingly, the copper(I) complexes of 2 were much less sensitive to oxidation. This might be a consequence of the steric crowding caused by the 6,6’-disubstitution of the bipyridine

• metal complexes’ host–guest chemistry at a later stage in a quantitative manner, however, a 1:2 metal-to-ligand stoichiometry like in the [Zn(1)2]-complexes is not very easy to study because one has to deal with a very complicated equilibrium between 1:2:2, 1:2:1, 1:2:0 and even more complicated metal

• dimeric complexes with 4,4'-disubstituted bipyridine 1. However, such a 1:2 effector–bipyridine ratio could lead to a difficult-to-handle host–guest chemistry when it comes to binding of additional guest molecules due to very complicated equilibria between 1:2:2, 1:2:1, 1:2:0 and even more complicated

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

• ][52], molecular machinery [53][54] and supramolecular host–guest chemistry [55][56]. With an angle of 120° between its aromatic moieties, it exhibits a rigid geometry with a defined alignment of functional groups (Figure 3, left). Next to classical convergent–concave structures, architectures with a

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

• functionalization of either its arene units or the bridged positions of its bicyclooctatriene system. This allows for the development of a range of structurally different triptycene-based derivatives [1]. Triptycene derivatives have also been used as building blocks for the synthesis of new molecules in host–guest

• chemistry. Moreover, they have been investigated for their potential applications in molecular recognition, showing powerful complexation abilities toward different kinds of organic guests [3][4]. Many biological processes, such as cell–cell communication, immune response and cancer metastasis, are

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

• chemistry and drug discovery as biosensing probes, in immunoassays and in host–guest chemistry [71]. Ferrocene-substituted amino acids have been of significant importance in the investigation of the secondary structures of different peptides and foldamers [72]. Thus, conjugates of the azido-functionalized β

Low-generation dendrimers with a calixarene core and based on a chiral C₂-symmetric pyrrolidine as iminosugar mimics

• Marco Marradi,
• Stefano Cicchi,
• Francesco Sansone,
• Alessandro Casnati and
• Andrea Goti

Beilstein J. Org. Chem. 2012, 8, 951–957, doi:10.3762/bjoc.8.107

• , such as calixarenes, with the advantages of a dendrimeric presentation of iminosugar analogues. Calixarenes [11] have been widely employed in host–guest chemistry, first as ligands for small ions and neutral molecules [12][13] and, more recently, for biologically relevant molecules and macromolecules

Enantioselective supramolecular devices in the gas phase. Resorcin[4]arene as a model system

• Caterina Fraschetti,
• Matthias C. Letzel,
• Antonello Filippi,
• Maurizio Speranza and
• Jochen Mattay

Beilstein J. Org. Chem. 2012, 8, 539–550, doi:10.3762/bjoc.8.62

• of tunable macrocycles largely studied in the context of host–guest chemistry, as cavitands [5] and capsules [6]. The great ability of resorcin[4]arenes to trap several classes of compounds makes them very suitable for the subtle study of the chemicophysical properties of their host–guest systems

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

• species. Applications in fields as diverse as ion selective electrode modifiers, fluorescence sensors, fullerene separations and biomimetic chemistry are described. Keywords: calixarenes; host–guest chemistry; macrocycles; oxacalixarenes; Introduction Calixarenes, macrocycles which are widely used in

• -substituted phenol; however, in host–guest chemistry an asymmetric macrocycle can provide a site for enantioselective molecular recognition. In the case of p-tert-butylcalix[n]arenes the tert-butyl substituent can be removed, as mentioned previously, through a retro-Friedel–Crafts acylation, and replaced by

Efficient, highly diastereoselective MS 4 Å-promoted one-pot, three-component synthesis of 2,6-disubstituted-4-tosyloxytetrahydropyrans via Prins cyclization

• Naseem Ahmed and
• Naveen Kumar Konduru

Beilstein J. Org. Chem. 2012, 8, 177–185, doi:10.3762/bjoc.8.19

• phorboxazoles (A and B) [1], (−)-centrolobine [2], GEX1A/herboxidiene [3], bryostatins [4], and pheromones [5] (Figure 1). Tetrahydropyran derivatives are also used as materials in photographic films [6] and host–guest chemistry [7]. In particular, 2,4,6-trisubstituted tetrahydropyrans have tremendous

On the mechanism of action of gated molecular baskets: The synchronicity of the revolving motion of gates and in/out trafficking of guests

• Keith Hermann,
• Stephen Rieth,
• Hashem A. Taha,
• Bao-Yu Wang,
• Christopher M. Hadad and
• Jovica D. Badjić

Beilstein J. Org. Chem. 2012, 8, 90–99, doi:10.3762/bjoc.8.9

• the basket: Specifically, the greater the affinity of the guest for occupying the basket, the less effective the gates are in “sweeping” the guest as the gates undergo their revolving motion. Keywords: dynamic NMR; host–guest chemistry; linear free-energy relationships; molecular encapsulation

PEG-embedded KBr₃: A recyclable catalyst for multicomponent coupling reaction for the efficient synthesis of functionalized piperidines

• Sanny Verma,
• Suman L. Jain and
• Bir Sain

Beilstein J. Org. Chem. 2011, 7, 1334–1341, doi:10.3762/bjoc.7.157

• poly(ethylene)glycol to prepare an efficient and highly stable tribromide reagent through the concept of host–guest chemistry. The prepared PEG-embedded tribromide was found to be a highly efficient catalyst for the synthesis of highly substituted piperidines in the one-pot coupling reaction of aniline