Synthesis and properties of fluorescent 4′-azulenyl-functionalized 2,2′:6′,2″-terpyridines

• Adrian E. Ion,
• Liliana Cristian,
• Mariana Voicescu,
• Masroor Bangesh,
• Augustin M. Madalan,
• Daniela Bala,
• Constantin Mihailciuc and
• Simona Nica

Beilstein J. Org. Chem. 2016, 12, 1812–1825, doi:10.3762/bjoc.12.171

• supramolecular interactions are observed in the crystal packing, via the azulene moieties and the terpyridine groups. In the crystal of 4a, the molecules are organized in columns running along the crystallographic a axis by π–π stacking interactions (3.39–3.64 Å). In the neighboring columns the molecular units

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

• isolated in high purity and extensively characterized by spectroscopic techniques. The in-depth analysis of the collected sets of NMR data resulted in the proposed models for the supramolecular interactions shown by the compounds. The isolated molecules can be applied in the fields of chemosensing and

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

• (i.e., Drosophila). Do we know so much about supramolecular interactions that all of the focus now should be on applications in biology, materials and medicine? The answer to this question is emphatically “No!” At a recent NSF workshop comprised of physical chemists and supramolecular chemists focused

Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities

• Carmen Mejuto,
• Beatriz Royo,
• Gregorio Guisado-Barrios and
• Eduardo Peris

Beilstein J. Org. Chem. 2015, 11, 2584–2590, doi:10.3762/bjoc.11.278

• nanoscale distance between the metals especially interesting [13][27] because for these systems a catalytic cooperation between the active metal sites should not be expected. As a consequence all catalytic improvements should be assigned to reasons dealing with supramolecular interactions [30] or with the

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

• -workers [188] have reported the synthesis of the naphthalene-diimide-based cyclophane 311 for understanding supramolecular interactions by metal ions (Figure 11). [3 + 2 + 1] Cycloaddition (Dötz benzannulation): In 2003, Wulff and co-workers [189] synthesized cyclophane derivatives using the Dötz

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• enhance structural and electronic properties as well as to introduce some “intelligent” functions such as conformational switchability and selectivity in terms of molecular recognition and supramolecular interactions. The synthesis of TTFV structures is usually carried out through a facile iodine-promoted

Multivalency as a chemical organization and action principle

• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 848–849, doi:10.3762/bjoc.11.94

• understanding of multivalent interactions this Thematic Series in the Beilstein Journal of Organic Chemistry puts its focus to unravel new cellular interactions that are highly relevant [2] and systematically combines theoretical exploration of defined multivalent supramolecular interactions [3] as well as new

Come-back of phenanthridine and phenanthridinium derivatives in the 21st century

• Lidija-Marija Tumir,
• Marijana Radić Stojković and
• Ivo Piantanida

Beilstein J. Org. Chem. 2014, 10, 2930–2954, doi:10.3762/bjoc.10.312

• phenanthridine derivatives resulted in the strong increase of the scientific interest about the turn of this century. Here are summarized phenanthridine-related advances in the 21st century (2000-present period) with emphasis on the supramolecular interactions and bioorganic chemistry, as well as novel or

End group functionalization of poly(ethylene glycol) with phenolphthalein: towards star-shaped polymers based on supramolecular interactions

• Carolin Fleischmann,
• Hendrik Wöhlk and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 2263–2269, doi:10.3762/bjoc.10.235

• ][45][46]. In this study, we present a new approach towards the preparation of star-shaped polymers that are formed through supramolecular interactions of β-CD and phenolphthalein. The great advantage of this system would be the possibility to follow the star polymer formation with naked eyes. Results

• and Discussion We herein describe the synthesis of the host and guest compound, which were further utilized for the preparation of star shaped polymers based on supramolecular interactions. The preparation of both, the host and the guest compound, occurred via 1,3-dipolar cycloaddition, in which the

• stable complexes based on supramolecular interactions between both compounds was proved by UV–vis measurements. Although DLS measurements did not succeed to explicitly validate the formation of the desired star shaped polymers due to the formation of strongly aggregated particles, we believe that this

Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

• Alexander Burkhart and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

• influenced significantly by supramolecular interactions with cyclodextrin [9]. Accordingly, we described in 2003 for the first time, that the LCST of a poly(N-adamantylacrylamide-co-N’-isopropylacrylamide) is influenced by CD [10]. Furthermore, the interaction of poly(pseudo-betaines) with CD leads to an

Macrocyclic bis(ureas) as ligands for anion complexation

• Claudia Kretschmer,
• Gertrud Dittmann and
• Johannes Beck

Beilstein J. Org. Chem. 2014, 10, 1834–1839, doi:10.3762/bjoc.10.193

• molecule” – is an area of modern chemistry, which has grown exponentially in the last decades [1][2]. Among the many concepts of supramolecular interactions, anion coordination chemistry has always been an intensively explored field, which still offers substantial progress [3][4][5]. The urea group has

Improving the reactivity of phenylacetylene macrocycles toward topochemical polymerization by side chains modification

• Simon Rondeau-Gagné,
• Jules Roméo Néabo,
• Maxime Daigle,
• Katy Cantin and
• Jean-François Morin

Beilstein J. Org. Chem. 2014, 10, 1613–1619, doi:10.3762/bjoc.10.167

• provide control over the size, shape and electronic properties of the resulting nanoarchitectures [1][2][3]. It is therefore not surprising that supramolecular interactions are regularly used to afford long-range molecular organization for organic and molecular electronics applications in which high-level

Influence of perylenediimide–pyrene supramolecular interactions on the stability of DNA-based hybrids: Importance of electrostatic complementarity

• Christian B. Winiger,
• Simon M. Langenegger,
• Oleg Khorev and
• Robert Häner

Beilstein J. Org. Chem. 2014, 10, 1589–1595, doi:10.3762/bjoc.10.164

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

• –vis region [25]. CT interactions have been employed to induce the supramolecular interactions between donors and acceptors, and lead to the formation of two-component organogels [26][27][28][29][30]. 18β-Glycyrrhetinic acid (GA, 1), a natural pentacyclic triterpenoid obtained from medicinal plants in

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• [5]. The Tc can be influenced for example through copolymerization with hydrophobic or hydrophilic comonomers and further through supramolecular interactions of these comonomers with cyclodextrins (CD) [6][7][8][9][10]. Generally, CDs are water soluble and their ability of forming inclusion complexes

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

• of hierarchical interactions to produce functional behaviour in molecular materials [4][5][6][7][8]; however, much remains to be investigated. In particular, designed supramolecular interactions that control the spatial and temporal distribution of materials are of interest [9][10][11][12]. Polymeric

• donor materials in blends with solution-processable fullerenes have produced the highest efficiency organic photovoltaic bulk heterojunction (BHJ) devices to date [13][14]. The critical role of supramolecular interactions together with material behaviour at interfaces has been significant in achieving

• these high efficiencies, as has been highlighted by the use of thermal annealing and solvent additives to produce dramatic efficiency increases [15]. In their role as systems for studying supramolecular interactions, polymers suffer from the added complexity of compositional factors such as molecular

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 crystal structure of the Dess–Martin periodinane

• Albert Schröckeneder,
• Desiree Stichnoth,
• Peter Mayer and
• Dirk Trauner

Beilstein J. Org. Chem. 2012, 8, 1523–1527, doi:10.3762/bjoc.8.172

• pair, which is engaged in supramolecular interactions (see below), the acetoxy substituents are pushed toward the phenyl ring. As a consequence, the iodine atom lies 0.315(1) Å below a plane formed by oxygens O1, O3, O5 and O7 and all iodine–oxygen bonds form an acute angle with the iodine–carbon bond

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

• that the addition of randomly modified β-cyclodextrin (RAME-β-CD) in aqueous medium could have a beneficial impact on the catalytic performances of phosphane-based aggregates in the Pd-catalyzed cleavage of allyl carbonates (Tsuji–Trost reaction). The RAME-β-CD/phosphane supramolecular interactions

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

• ) by their coupling to azobenzene dyes allowing them to serve as colorimetric indicators for supramolecular interactions. Beyond reporting the straightforward coupling of DAN and DeUG to azobenzene dyes, we show that the dye-recognition-unit conjugates act as selective polymer colorants (Figure 2). The

• temperature. Chemical structures of UPy dimer and DAN complexes with UG and DeUG. Illustration of the use of DeUG-Dye and DAN-Dye as colorimetric indicators for supramolecular interactions through specific quadruply hydrogen-bonding interactions. Top: DeUG-Dye interacts with DAN modified polystyrene (PS

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

• displayed higher transition temperatures and a wider mesophase range than the free ligand, as determined from DSC and POM experiments. Unfortunately, no phase assignments were made by diffraction methods, precluding the determination of either the supramolecular interactions of the ligands or the positional

Effects of anion complexation on the photoreactivity of bisureido- and bisthioureido-substituted dibenzobarrelene derivatives

• Heiko Ihmels and
• Jia Luo

Beilstein J. Org. Chem. 2011, 7, 278–289, doi:10.3762/bjoc.7.37

• derivatives; Introduction The control of the selectivity of a photoreaction by supramolecular interactions has recently received much attention [1][2][3]. For example, chiral receptors have been employed that associate with photoreactive substrates, leading to a distinct preferential conformation of the

• challenge to develop a method to accomplish stereoselective DPM rearrangements of dibenzobarrelene derivatives in homogenous solutions. Therefore, we intended to study whether supramolecular interactions of chiral additives with achiral dibenzobarrelenes may be used to influence the photoreactivity of the

• systematically to influence the photochemical properties of a substrate, although such supramolecular receptor–anion interactions have been used in the organocatalysis of ground-state reactions [40][41][42][43][44]. It should be noted that the supramolecular interactions between anions and ureido- or thioureido

Exceptionally small supramolecular hydrogelators based on aromatic–aromatic interactions

• Junfeng Shi,
• Yuan Gao,
• Zhimou Yang and
• Bing Xu

Beilstein J. Org. Chem. 2011, 7, 167–172, doi:10.3762/bjoc.7.23

• -based hydrogelators suggests that a single amino acid molecule is unlikely to be able to provide an adequate amount of supramolecular interactions to form nanofibers, entrap the solvent, and result in hydrogelation. Apparently, the cinnamoyl group is the minimum structure motif to provide sufficient

Oxalyl retro-peptide gelators. Synthesis, gelation properties and stereochemical effects

• Janja Makarević,
• Milan Jokić,
• Leo Frkanec,
• Vesna Čaplar,
• Nataša Šijaković Vujičić and
• Mladen Žinić

Beilstein J. Org. Chem. 2010, 6, 945–959, doi:10.3762/bjoc.6.106

• interactions of enantiomers that lead to diasteromeric assemblies with a certain level of organization. FTIR, 1H NMR and CD investigations To identify supramolecular interactions that stabilize gel assemblies, the selected gels were studied by 1H NMR, FTIR and CD spectroscopy. Valuable information on the self

Chiral gels derived from secondary ammonium salts of (1R,3S)-(+)-camphoric acid

• Tapas Kumar Adalder,
• N. N. Adarsh,
• Ravish Sankolli and
• Parthasarathi Dastidar

Beilstein J. Org. Chem. 2010, 6, 848–858, doi:10.3762/bjoc.6.100

• temperature) vs [gelator] plots on some selected gels displayed a steady increase of Tgel with the increase in [gelator] which indicated that, in the present cases, self-assembly in the gel state was driven by strong supramolecular interactions such as hydrogen bonding. Application of the Schroeder-van Laar