Economical and scalable synthesis of 6-amino-2-cyanobenzothiazole

• Jacob R. Hauser,
• Hester A. Beard,
• Mary E. Bayana,
• Katherine E. Jolley,
• Stuart L. Warriner and
• Robin S. Bon

Beilstein J. Org. Chem. 2016, 12, 2019–2025, doi:10.3762/bjoc.12.189

• nanostructures in cellulo [12][13]. The precursor of D-aminoluciferin, 6-amino-2-cyanobenzothiazole (ACBT, 8), is an attractive building block for BLI probes and for handles for CBT ligations, because of the ease of derivatisation of its amino group. Like other functionalised CBTs, ACBT is available from

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• upon in the creation of two new macrocycles. First, cyanostars are larger and like to capture large anions. Second is tricarb, which also favors large anions but shows a propensity to self-assemble in an orderly and stable manner, laying a foundation for future designs of hierarchical nanostructures

• design. The long-term ramifications include the ability to create semiconductor structures by simple self-assembly. Thus, the goal is to contribute scientific understanding on how to program the nanostructures of advanced technology by employing bottom-up molecular design. The design and building of a

Aggregation behavior of amphiphilic cyclodextrins in a nonpolar solvent: evidence of large-scale structures by atomistic molecular dynamics simulations and solution studies

• Giuseppina Raffaini,
• Fabio Ganazzoli and
• Antonino Mazzaglia

Beilstein J. Org. Chem. 2016, 12, 73–80, doi:10.3762/bjoc.12.8

• , Farmaceutiche ed Ambientali dell’Università di Messina, V. le F. Stagno d'Alcontres 31, 98166 Messina, Italy 10.3762/bjoc.12.8 Abstract Chemically modified cyclodextrins carrying both hydrophobic and hydrophilic substituents may form supramolecular aggregates or nanostructures of great interest. These systems

• particular at longer lengths. In any case, these nanostructures are stable at least from the kinetic viewpoint for relatively long times thanks to the large number of intermolecular interactions of dipolar and dispersive nature. The dynamic light scattering experiments indicate the presence of aggregates

• scattering investigations show that, indeed also in a nonpolar solvent such as dichloromethane, these amphiphilic cyclodextrins give rise to quite well defined aggregates, or nanostructures, having a hydrodynamic radius of about 80 nm and a relatively modest polydispersity. This result obtained with a

Aggregation behaviour of amphiphilic cyclodextrins: the nucleation stage by atomistic molecular dynamics simulations

• Giuseppina Raffaini,
• Antonino Mazzaglia and
• Fabio Ganazzoli

Beilstein J. Org. Chem. 2015, 11, 2459–2473, doi:10.3762/bjoc.11.267

• their versatility both as drug carriers [11][14][15] and as self-assembling systems for molecular recognition [16][17][18]. Different research groups investigated the aCD behaviour in solution, elucidating their nanostructures and physicochemical behaviour, including the temperature- and concentration

Urethane tetrathiafulvalene derivatives: synthesis, self-assembly and electrochemical properties

• Xiang Sun,
• Guoqiao Lai,
• Zhifang Li,
• Yuwen Ma,
• Xiao Yuan,
• Yongjia Shen and
• Chengyun Wang

Beilstein J. Org. Chem. 2015, 11, 2343–2349, doi:10.3762/bjoc.11.255

• units and urethane groups (Figure 1). The combination of the urethane group (forming hydrogen bonds) and the TTF unit (forming π–π stacking) may promote the formation of nanostructures. To the best of our knowledge, urethane groups have been rarely introduced into the molecular structure of TTF

Star-shaped tetrathiafulvalene oligomers towards the construction of conducting supramolecular assembly

• Masahiko Iyoda and
• Masashi Hasegawa

Beilstein J. Org. Chem. 2015, 11, 1596–1613, doi:10.3762/bjoc.11.175

• nanostructures. Although radical cations derived from TTF oligomers strongly interact in solution to produce a mixed-valence dimer and π-dimer, it seems to be difficult to produce nanoobjects of radical cations different from those of neutral TTF oligomers. In some cases, however, radical cations form

• -active nanostructures in the solid state were summarized so far. Therefore, this review focuses on the conducting nanostructures of TTF derivatives in the solid state, together with association behavior in solution. Review Redox-active radially expanded TTF oligomers in solution and the solid state TTF

• ) are also employed for determining the conductivities of nanoobjects [50][51]. The electrical conductivity of nanostructures mainly depends on the alignment of stacked TTFs or their radical salts. The first fibrous material was fabricated by using arborol-TTF 11 in 1994 by Joergensen, Bechgaard, and co

Terminal lipophilization of a unique DNA dodecamer by various nucleolipid headgroups: Their incorporation into artificial lipid bilayers and hydrodynamic properties

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2015, 11, 913–929, doi:10.3762/bjoc.11.103

• complex nanoarchitectures [33][34], the interaction of such nanostructures with lipid membranes [35][36][37][38], as well as the optimization of the in vivo delivery of lipophilic siRNA [10][11][12] (e.g., by DNA trafficking [7]). Further studies from our group will include the binding of terminally

Impact of multivalent charge presentation on peptide–nanoparticle aggregation

• Daniel Schöne,
• Boris Schade,
• Christoph Böttcher and
• Beate Koksch

Beilstein J. Org. Chem. 2015, 11, 792–803, doi:10.3762/bjoc.11.89

• ] interactions have been explored. In particular, peptide-based assemblies afford numerous advantages such as the modification of nanostructures by mutations of the primary sequence of peptides which may lead to the formation of various hierarchical morphologies [23][24][25]. The strategies for the assembly of

Discrete multiporphyrin pseudorotaxane assemblies from di- and tetravalent porphyrin building blocks

• Mirko Lohse,
• Larissa K. S. von Krbek,
• Sebastian Radunz,
• Suresh Moorthy,
• Christoph A. Schalley and
• Stefan Hecht

Beilstein J. Org. Chem. 2015, 11, 748–762, doi:10.3762/bjoc.11.85

• stoichiometry, while the amount of alternative structures can be neglected. Our results illustrate the power of multivalency to program the multicomponent self-assembly of specific entities into discrete functional nanostructures. Keywords: crown ethers; multicomponent assembly; multivalency; porphyrins

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• mediated by a multivalent interaction between HA binding pockets and cell surface receptors as a monovalent interaction is too weak for stable binding [10][11]. Peptide-based self-assembled nanostructures can be used as the simplest platform for the multivalent display of ligands, although this approach

• (TEM). First, the size of the supramolecular nanostructures formed by C18-PeBGF, C18-s2s, and C18-rs2s was analyzed by DLS at low concentration of 20 µM in PBS (10 mM, pH 7.4). For the analysis of C18-PeBGF, we observed a hydrodynamic diameter of 16.7 nm (PDI = 0.454) along with 10–15% bigger

• virus binding ligands with enhanced antiviral activity. Although DLS analysis indicated the presence of nanostructures at lower concentrations, as the majority of detected objects showed an average diameter of 16.7 nm, we found already at 20 µM concentrations the formation of rather large supramolecular

Properties of cationic monosubstituted tetraalkylammonium cyclodextrin derivatives – their stability, complexation ability in solution or when deposited on solid anionic surface

• Martin Popr,
• Sergey K. Filippov,
• Nikolai Matushkin,
• Juraj Dian and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2015, 11, 192–199, doi:10.3762/bjoc.11.20

• acid [26]. Similar approaches of ionic self-assembly with CDs were used for the preparation of nanoparticles with external CD trigger [27], new material nanostructures [28], polyelectrolyte-surfactant complexes which yield new types of solid mesomorphous materials [29], or membranes with size-selective

Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

• Joscha Vollmeyer,
• Friederike Eberhagen,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2014, 10, 2774–2782, doi:10.3762/bjoc.10.294

• ; solid/liquid interface; supramolecular surface patterning; template; Introduction One of the ultimate aims in supramolecular chemistry on solid surfaces is the formation of two-dimensional (2D) nanostructures that are capable of performing highly specific tasks as an effect of functional units that are

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum and
• Bing Xu

Beilstein J. Org. Chem. 2014, 10, 2406–2413, doi:10.3762/bjoc.10.250

• ], Fmoc [23][24], lipid [25]), it is still challenging to judge which molecules could self-assemble to form ordered nanostructures. This challenge requires the molecular engineering of the conjugates and intense study of their properties to provide a molecular basis for the understanding of the

Autonomous assembly of synthetic oligonucleotides built from an expanded DNA alphabet. Total synthesis of a gene encoding kanamycin resistance

• Kristen K. Merritt,
• Kevin M. Bradley,
• Daniel Hutter,
• Mariko F. Matsuura,
• Diane J. Rowold and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 2348–2360, doi:10.3762/bjoc.10.245

• molecules” strategy mentioned above, the United States Army Research Office in 2011 issued a small business grant solicitation seeking software to allow 30,000 base pairs of single-stranded DNA to self-assemble to form nanostructures. In 2012, DARPA issued a small business grant solicitation seeking

Specific DNA duplex formation at an artificial lipid bilayer: fluorescence microscopy after Sybr Green I staining

• Emma Werz and
• Helmut Rosemeyer

Beilstein J. Org. Chem. 2014, 10, 2307–2321, doi:10.3762/bjoc.10.240

• ability to form complex nano-architectures [5][6] as well as self-assembling aggregates such as micelles, vesicles [3] and bilayer formation of nucleolipids [7] offers numerous possibilities, e.g., for drug delivery [3]. Simultaneously, the interaction of such nanostructures with lipid membranes becomes

• ], 2. for the development of analytical techniques for the detection of nucleic acids [15][16][17], 3. for structure elucidation of complex aggregates formed by such natural nanostructures [5][6] and 4. for cell-surface engineering [18]. In a preceding manuscript [19] we reported the lipid bilayer

OligArch: A software tool to allow artificially expanded genetic information systems (AEGIS) to guide the autonomous self-assembly of long DNA constructs from multiple DNA single strands

• Kevin M. Bradley and
• Steven A. Benner

Beilstein J. Org. Chem. 2014, 10, 1826–1833, doi:10.3762/bjoc.10.192

• solicitation seeking companies to design software to design 30,000 base pairs of single stranded DNA that would autonomously self-assemble to form nanostructures. In 2012, DARPA issued a small business grant solicitation seeking technology to assemble single-stranded synthetic fragments to give 20,000 base

Pyrene-modified PNAs: Stacking interactions and selective excimer emission in PNA₂DNA triplexes

• Alex Manicardi,
• Lucia Guidi,
• Alice Ghidini and
• Roberto Corradini

Beilstein J. Org. Chem. 2014, 10, 1495–1503, doi:10.3762/bjoc.10.154

• ][15][16][17][18][19][20]. Furthermore, pyrene has been shown to favour self-assembly processes of supramolecular structures [21][22][23][24][25][26][27][28] and interact with carbon nanostructures such as nanotubes [29] or graphene [30], thus allowing to create composite material with special

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• tapping mode in air. The contact mode of scanning was used for experiments in a liquid cell. Experiments in a liquid cell allowed us to study the kinetics of the process without a possible distortion of the nanostructures resulting from the drying of the sample. The Raman spectra (Figure 3) of biantennary

Homochiral BINOL-based macrocycles with π-electron-rich, electron-withdrawing or extended spacing units as receptors for C₆₀

• Marco Caricato,
• Silvia Díez González,
• Idoia Arandia Ariño and
• Dario Pasini

Beilstein J. Org. Chem. 2014, 10, 1308–1316, doi:10.3762/bjoc.10.132

• cyclic adducts exhibit recognition properties towards C60 in toluene solutions (up to log Ka = 3.2) with variable stoichiometries and variable intensities of the charge-tranfer band upon complexation. Keywords: BINOL; C60; carbon nanomaterials; carbon nanostructures; chirality; macrocycles; sensors

A new building block for DNA network formation by self-assembly and polymerase chain reaction

• Holger Bußkamp,
• Sascha Keller,
• Marta Robotta,
• Malte Drescher and
• Andreas Marx

Beilstein J. Org. Chem. 2014, 10, 1037–1046, doi:10.3762/bjoc.10.104

• in many nanotechnological approaches. Inspired by naturally existing self-assembled DNA architectures, branched DNA has been developed that allows self-assembly to predesigned architectures with dimensions on the nanometer scale. DNA is an attractive material for generation of nanostructures due to a

• then several reports have described the generation of bDNAs self-assembling to predesigned architectures with dimensions on the nanometer scale [5][6][7][8][9]. Based on this, numerous examples of 2D arrays [10][11][12][13][14], DNA origami [15] and complex 3D DNA nanostructures [16][17][18][19][20

• -free translation system [30]. Recently, ordered 2D DNA scaffolds were reported in which a nanometer precise arrangement of enzymes on these scaffolds leads to efficient enzymatic communication [31]. DNA polymerases have been applied for the assembly of DNA nanostructures. Joyce et al. employed a DNA

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

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

• gel formation at the highest concentrations, indicating the formation of high-aspect-ratio nanofibers in solution [33]. Films drop cast from 1 mg/mL and 10 mg/mL solutions of 2 in chloroform were investigated by AFM in order to directly observe any nanostructures present. A representative scan at each

• concentration is shown in Figure 4. The films were found to contain interconnected fibrous nanostructures approximately 85–110 nm in width at both concentrations; however, the structures appeared to be more regular in films cast from solutions at higher concentrations. Hydrogen-bond-mediated self-association of

• of nanostructures as observed by AFM and the gelation behaviour at high concentration. Alternatively, isodesmic self-association to form one dimensional hydrogen-bonded chains of 2 may incur conformational changes in 2 for steric reasons, which could result in changes to the 1H chemical shifts of 2

The conjugation of nonsteroidal anti-inflammatory drugs (NSAID) to small peptides for generating multifunctional supramolecular nanofibers/hydrogels

• Jiayang Li,
• Yi Kuang,
• Junfeng Shi,
• Yuan Gao,
• Jie Zhou and
• Bing Xu

Beilstein J. Org. Chem. 2013, 9, 908–917, doi:10.3762/bjoc.9.104

• self-assembly in water. Transmission electron microscopy (TEM) In addition to the macroscopic phase transition such as hydrogelation, another hallmark of molecular self-assembly in water is the formation of ordered nanostructures (e.g., nanofibers or nanoparticles). As revealed by the TEM images

• 2a comprises two kinds of nanostructures, i.e., nanofibers and nanoparticles, visible in the TEM images. As shown in Figure 2E, long nanofibers with an average width of 17 nm entangle together to form larger helical nanofibers with an average width of 30 nm. Higher-magnification TEM shows that the

• nanofibers with an average width of 12 nm (Figure 2F). Interestingly, the TEM of the hydrogel of 3a presents similar nanostructures to those in the hydrogel of 2b. As shown in Figure 2G, the long uniform nanofibers in the hydrogel of 3a have an average width of 12 nm. Higher magnification of the TEM of the

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

• Daniel Fürniss,
• Timo Mack,
• Frank Hahn,
• Sidonie B. L. Vollrath,
• Katarzyna Koroniak,
• Ute Schepers and
• Stefan Bräse

Beilstein J. Org. Chem. 2013, 9, 56–63, doi:10.3762/bjoc.9.7

• D.F.), Theodor Laymann Foundation (fellowships to T.M. and F.H.), the Fonds der Chemischen Industrie, the SFB 645 (Project Z1), the Helmholtz Program “Biointerface” and the Center for Functionalized Nanostructures (CFN), Karlsruhe.

The effect of the formyl group position upon asymmetric isomeric diarylethenes bearing a naphthalene moiety

• Renjie Wang,
• Shouzhi Pu,
• Gang Liu and
• Shiqiang Cui

Beilstein J. Org. Chem. 2012, 8, 1018–1026, doi:10.3762/bjoc.8.114

• . reported an amphiphilic molecule with hydrophilic and hydrophobic chains on two ends of a rigid diarylethene core. This compound can form stable vesicle nanostructures in aqueous solution, and exhibits excellent switchable fluorescence between open and closed states in the living cells, with low