Supramolecular frameworks based on [60]fullerene hexakisadducts

• Andreas Kraft,
• Johannes Stangl,
• Ana-Maria Krause,
• Klaus Müller-Buschbaum and
• Florian Beuerle

Beilstein J. Org. Chem. 2017, 13, 1–9, doi:10.3762/bjoc.13.1

• structure of dodecaacid C2 (Cn stands for Th symmetrical hexakisadducts C60{C[COO(CH2)n−1COOH]2}6, see Figure 1) revealing a complex hydrogen-bonding network in the crystalline state [57]. Based on this initial finding, we also utilized C2 and elongated derivative C3 as organic connectivity centers in metal

• crystallization of C3 and also synthesized the next homologue C4 starting from malonate 1 [59] according to a standard two-step protocol via a sixfold Bingel reaction followed by acidic deprotection (Scheme 1). As we observed the insertion of MeOH molecules into the hydrogen-bonding network of HFF-1 [57], we also

• top view indicating enlarged intralayer spacing for elongated derivatives (bottom); images are created with PyMOL [58]. Hydrogen bonding network for HFF-3 (left, hydrogen bonds yellow) and porous channels along the c axis filled with unbound Et2O molecules (right, Et2O orange, inner pore surface

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

• , the knowledge of the binding constants (Kass) is crucial because these values provide an index of host–guest binding forces. CDs can also form exclusion complexes where the CDs are bound to the guest through a H-bond network. For instance, the complexation of [PMo12O40] anion by β- and γ-CD results in

Towards the development of continuous, organocatalytic, and stereoselective reactions in deep eutectic solvents

• Davide Brenna,
• Elisabetta Massolo,
• Alessandra Puglisi,
• Sergio Rossi,
• Giuseppe Celentano,
• Maurizio Benaglia and
• Vito Capriati

Beilstein J. Org. Chem. 2016, 12, 2620–2626, doi:10.3762/bjoc.12.258

• possible interaction between the aldol product and the DES network (Figure 1). Due to its favourable physical and mechanical properties, DES A was selected for the initial screening of the different experimental conditions in continuo. The first experimental set-up that was studied (Figure 1, I) was built

Enzymatic synthesis and phosphorolysis of 4(2)-thioxo- and 6(5)-azapyrimidine nucleosides by E. coli nucleoside phosphorylases

• Vladimir A. Stepchenko,
• Anatoly I. Miroshnikov,
• Frank Seela and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2016, 12, 2588–2601, doi:10.3762/bjoc.12.254

• (=O) of uracil and the hydrogen bonds network of the side-chains of Gln166, Arg223 and Arg168 are responsible for the strict specificity to uracil and to a lesser extent to thymine [5][6] recognizing the 2C(=O)-3N(H)-4C(=O) fragment as distinct from the 2C(=O)-3N=4C(NH2) part of cytosine. Notably, the

Synthesis of three-dimensional porous hyper-crosslinked polymers via thiol–yne reaction

• Mathias Lang,
• Alexandra Schade and
• Stefan Bräse

Beilstein J. Org. Chem. 2016, 12, 2570–2576, doi:10.3762/bjoc.12.252

• metal-free reaction conditions, high yields and easy purification. Results and Discussion The first network shown here was synthesized by crosslinking the two tetrahedral tetraphenylmethane core structures 1 and 2 via the radical-mediated thiol–yne reaction using AIBN as initiator. The second network

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• computational investigations. Acknowledgements M. Decker gratefully acknowledges the German Science Foundation (Deutsche Forschungsgemeinschaft) for financial support (DFG DE1546/6-1 and DE1546/6-3) and the Elite Network of Bavaria for awarding a Ph.D. position to A. Drakopoulos within the International

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• COP-156-amine showed fast and increased CO2 uptake under simulated moist flue gas conditions compared to the starting network and usual industrial CO2 solvents, reaching up to 7.8 wt % uptake at 40 °C. Keywords: C–C bond; CO2 capture; microporous materials; porous polymers; postmodification

• ; Findings Porous polymers are network polymers that are made from multivalent monomers and form permanent pores through the net formation [1]. They differ slightly from cross-linked polymers with more certainty in the location of branching and the type and quantity of functionalities. Also, the rigidity of

• , cyanovinylene bridged porous networks are not studied extensively and our previously reported COP-100 structure [18] suffered from low porosity. In order to obtain a cyanovinylene-bridged porous network with tangible surface area, different core and linker combinations were tested leading to the synthesis of

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• HCP-94 was 342 mL/g (Figure 2b). Both low temperature N2 adsorption isotherms were of type-I category and a hysteresis was observed in desorption profiles. The hysteresis in the desorption curves can be explained in terms of a network swelling in the presence of condensed nitrogen [34]. The Howarth

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• polymer, without an activation step, removed 20% of the total metal load in spiked solutions (SS) containing five metals at 10 mg·L−1 each. This could be attributed to surface adsorption and diffusion into the polymer network. However, it was observed that an activation step in an aqueous solution of

• -linking agent BTCA was used, this compound presents four carboxylic functions and a previous study [18] showed that only two of its carboxylic groups reacted with the CD units to form the polymer network, the two remaining ones being available to react with cations through chemisorption (electrostatic

• precipitation and/or physical phenomena (surface adsorption, diffusion into the network and/or hydrogen bonding). This study demonstrated the efficiency of activated polyBTCA-CD to treat the inorganic load, but also to treat the organic pollutants. It can be noted that the analysis of 26 substances present in

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• quite surprised to find that we generated regular spherical and network structures (Figure 3) [24]. This "bricks and mortar" assembly process provides a modular system where structure and stoichiometry of the components drives structure formation. These assemblies set us on a path of generating

Star-shaped and linear π-conjugated oligomers consisting of a tetrathienoanthracene core and multiple diketopyrrolopyrrole arms for organic solar cells

• Hideaki Komiyama,
• Chihaya Adachi and
• Takuma Yasuda

Beilstein J. Org. Chem. 2016, 12, 1459–1466, doi:10.3762/bjoc.12.142

• Scientific Research (Nos. 16K21218 (H.K.) and 15H01049 (T.Y.)) from JSPS, the Cooperative Research Program of “Network Joint Research Center for Materials and Devices”, the Yoshida Education and Foundation (H.K.), the Yashima Environment Technology Foundation (T.Y.), and the KDDI Foundation Research Grant

Discovery of an inhibitor of the production of the Pseudomonas aeruginosa virulence factor pyocyanin in wild-type cells

• Bernardas Morkunas,
• Balint Gal,
• Warren R. J. D. Galloway,
• James T. Hodgkinson,
• Brett M. Ibbeson,
• Yaw Sing Tan,
• Martin Welch and
• David R. Spring

Beilstein J. Org. Chem. 2016, 12, 1428–1433, doi:10.3762/bjoc.12.137

• network with the Las system at the top of the network. The regulator of the pyocyanin biosynthesis genes is RhlR and transcription of the rhlR gene is itself regulated by LasR. Hence, it has been hypothesised that LasR inhibition should result in the attenuation of pyocyanin production [8][9][20]. This

• studies have demonstrated that the straight forward hierarchical QS network (with the las system at the forefront followed by the lower ranked rhl and pqs signalling system) is more elaborate and complex than this hierarchical structure [8][9][30]. Taking these studies into account it is possible that

From N-vinylpyrrolidone anions to modified paraffin-like oligomers via double alkylation with 1,8-dibromooctane: access to covalent networks and oligomeric amines for dye attachment

• Daniela Obels,
• Melanie Lievenbrück and
• Helmut Ritter

Beilstein J. Org. Chem. 2016, 12, 1395–1400, doi:10.3762/bjoc.12.133

• water swellable network 3a and 3b. Photographs of water-swollen polymer disks consisting of 1 mol % (3a) and 2.5 mol % (3b) of 2a as cross linker. UV–vis spectra of oligomers 5 (c = 0.16 g/mL, red), 6 (c = 0.63 g/mL, blue) and DFA (c = 0.016 g/mL, grey). Alkylation of N-VP with 1,8-dibromooctane

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

• Svetlana V. Vasilyeva,
• Vyacheslav V. Filichev and
• Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

• and the New Zealand Ministry of Research, Science and Technology for their support with the Dumont d’Urville network grant (EGIDE No 18961YF). We thank Prof. Tom Brown for a gift of THPTA, Dr. Marie-Paule Teulade-Fichou for coumarine M14, Drs. Alain Blond, Arul Marie and Mr. Lionel Dubost for NMR and

Antibiotics from predatory bacteria

• Juliane Korp,
• María S. Vela Gurovic and
• Markus Nett

Beilstein J. Org. Chem. 2016, 12, 594–607, doi:10.3762/bjoc.12.58

• , requires a tight regulatory network in predatory myxobacteria [80]. This is also reflected in the genome of M. xanthus DK1622, which features an unusual high duplication frequency of genes encoding regulatory proteins like serine-threonine kinases and enhancer binding proteins (EBPs) [43]. EBPs are

• myxobacterium. The findings of this study attested a complex regulatory network to M. xanthus DK1622, in which development, predation, and motility are clearly connected to secondary metabolism [84]. Lastly, it should be mentioned that genomic data might also provide the explanation for the predatory behavior

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• Initial Training Network, Project No 608407 (CyclonHit) and OTKA PD 109373 are greatly acknowledged.

Effective in silico prediction of new oxazolidinone antibiotics: force field simulations of the antibiotic–ribosome complex supervised by experiment and electronic structure methods

• Jörg Grunenberg and
• Giuseppe Licari

Beilstein J. Org. Chem. 2016, 12, 415–428, doi:10.3762/bjoc.12.45

• explicitly if they were part of the hydrogen bond network. This working shell was the starting point for the construction of all complexes models used during our MC scans. It includes linezolid, the CCA-N-Phe unit, nucleotides belonging to the r-RNA backbone, a few amino acids, water molecules and cations

Self and directed assembly: people and molecules

• Tony D. James

Beilstein J. Org. Chem. 2016, 12, 391–405, doi:10.3762/bjoc.12.42

• [80] and the CASE Network was established [81][82][83]. “A scientist has to work very hard to get to the point where he can be lucky.” – Robert B. Woodward (1917–1979) The 7th Catalysis and Sensing for our Environment Symposium was held in Dublin on 9–10 July 2015 and jointly hosted in Ireland by

• Network [85]. Thanks to the CASE Network enduring collaborations have been established in China with outstanding academics including Yun-Bao Jiang [86][87][88][89][90][91][92][93], Xuhong Qian [94][95][96], Yitao Long [97][98][99][100][101][102][103][104][105][106], Weiping Deng [107] ,Weihong Zhu [108

• . I would particularly like to thank The Catalysis and Sensing for our Environment (CASE) network [83] for providing excellent networking opportunities, since many of the results contained in this personal perspective are a direct result of the network.

Art, auto-mechanics, and supramolecular chemistry. A merging of hobbies and career

• Eric V. Anslyn

Beilstein J. Org. Chem. 2016, 12, 362–376, doi:10.3762/bjoc.12.40

• acids, we could create an IDA that correlated with the age of the whisky. In a second similar study, we took advantage of our early fledgling interest in chemometrics (see more below), and showed how an artificial neural network (ANN) could be used to analyze mixtures of cross-reactive receptors with

Interactions of cyclodextrins and their derivatives with toxic organophosphorus compounds

• Sophie Letort,
• Sébastien Balieu,
• William Erb,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2016, 12, 204–228, doi:10.3762/bjoc.12.23

• be due to the presence of a strong hydrogen bond network between the secondary hydroxy groups, which restricts their degree of liberty, and lets them to relay the active radicals toward the phosphorus atom. Hydrolysis of chemical warfare agents Accelerating nerve agent’s hydrolysis, CDs are

Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

• Javier Ajenjo,
• Martin Greenhall,
• Camillo Zarantonello and
• Petr Beier

Beilstein J. Org. Chem. 2016, 12, 192–197, doi:10.3762/bjoc.12.21

• copies of NMR spectra. Acknowledgements This work was supported by the Academy of Sciences of the Czech Republic (Research Plan RVO: 61388963) and by the Initial Training Network, FLUOR21, funded by the FP7 Marie Curie Actions of the European Commission (FP7-PEOPLE-2013-ITN-607787).

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

• ] and dendrimers [64][65] – work that ultimately led Cyrus Anderson, Darrell Kuykendall, Ying Li, Taiho Park, Kwansima Quansah, and Mauricio Suarez to a broader range of supramolecular polymers, including liquid crystals [66], network blends [67], alternating copolymers [68], reversible adhesives [69

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

• -CD:n-C18H37 solution probably as a result of the larger γ-CD simultaneously complexing both n-C18H37 and SDS such that complexation of two n-C18H37 by γ-CD is minimized (Figure 5c). 2 Network assembly by cyclodextrin- and guest-substituted polymers The ability of cyclodextrins to complex hydrophobic

• between polymer chains which may be exploited to modulate the polymer networks formed and the viscosities of their aqueous solutions. 2.1 Construction of polymer networks The formation of a polymer network through host–guest complexation between cyclodextrin and hydrophobic substituents on different

• polymer chains is illustrated in a general manner in Figure 6. Such network formation is exemplified by the research of Wenz et al. in which mixtures of poly(maleic acid)-co-(isobutene) copolymers substituted with either β-CD or 4-tert-butylanilide form viscous aqueous solutions as host–guest complexation

Polydisperse methyl β-cyclodextrin–epichlorohydrin polymers: variable contact time ¹³C CP-MAS solid-state NMR characterization

• Isabelle Mallard,
• Davy Baudelet,
• Franca Castiglione,
• Monica Ferro,
• Walter Panzeri,
• Enzio Ragg and
• Andrea Mele

Beilstein J. Org. Chem. 2015, 11, 2785–2794, doi:10.3762/bjoc.11.299

• template introduces highly specific sites into the polymeric network and, after removal of the target the polymer is able to rebind the molecule with high selectivity. Polymers of CRYSMEB were synthesized according to the procedure of Mallard Favier [22]. Our synthetic protocol was chosen to employ a

• globular polymers and the linear polymer network promotes a more efficient guest binding due to a more effective accessibility of the cavity. These points allow an easy removal of toluene by simple drying in the oven under vacuum. Additionally, the control of the polymer growth leading to linear polymer

• network provided a sufficiently regular system for the interpretation of the NMR results. Due to the experimental conditions such as high NaOH concentration, high EP/CD ratio and high temperature [15][35], the polymerization process leads exclusively to insoluble cross-linked polymers after EP addition

Recent advances in metathesis-derived polymers containing transition metals in the side chain

• Ileana Dragutan,
• Valerian Dragutan,
• Bogdan C. Simionescu,
• Albert Demonceau and
• Helmut Fischer

Beilstein J. Org. Chem. 2015, 11, 2747–2762, doi:10.3762/bjoc.11.296

• -bonding modes arise in the supramolecular polymeric network, i.e., an intramolecular H bonding with the β- and γ-phosphate groups of ATP2− and an intermolecular H bond between the α-phosphate and another amidoferrocenyl group. Redox properties of polycationic copolymers containing the complex [Fe(η5-C5H5