Particle size effect in the mechanically assisted synthesis of β-cyclodextrin mesitylene sulfonate

• Stéphane Menuel,
• Sébastien Saitzek,
• Eric Monflier and
• Frédéric Hapiot

Beilstein J. Org. Chem. 2020, 16, 2598–2606, doi:10.3762/bjoc.16.211

• different milling times. As can be seen from Figure 1, the powder particles experience comminution and decrease in size over time and after grinding for 10 min, β-CD displays microsized particles (Figure 1c). Longer grinding times led to particles with sizes below 300 nm in diameter (Figure 1d and Figure 1e

• . From the SEM images and using the ImageJ software, we were able to determine the size of the β-CD particles and the calculated Feret mean diameter (mean value of the Feret diameters over all orientations, i.e., 0–180°) are collected in Table 1. BET analysis The β-CD particle size was also confirmed by

• (290 mg, 1.32 mmol) were placed in a 10 mL zirconium oxide reactor containing one zirconium oxide ball of 9 mm diameter. The solid mixture was shaken for 5 min at 30 Hz. Shaking was then stopped for 5 min. The procedure was repeated 54 times for a total grinding time of 270 min. The reactor was opened

A new method for the synthesis of diamantane by hydroisomerization of binor-S on treatment with sulfuric acid

• Rishat I. Aminov and
• Ravil I. Khusnutdinov

Beilstein J. Org. Chem. 2020, 16, 2534–2539, doi:10.3762/bjoc.16.205

• mL/min)]. The sonication was carried out with an ultrasound generator IL10–0.63 (INLAB LTD) for 180 min at a frequency of 22 kHz with a submerged 15 mm diameter titanium horn, with output power 150 W. The reactions were carried out in a 100 × 35 mm glass reactor equipped with a jacket to maintain the

Dawn of a new era in industrial photochemistry: the scale-up of micro- and mesostructured photoreactors

• Emine Kayahan,
• Mathias Jacobs,
• Leen Braeken,
• Leen C.J. Thomassen,
• Simon Kuhn,
• Tom van Gerven and
• M. Enis Leblebici

Beilstein J. Org. Chem. 2020, 16, 2484–2504, doi:10.3762/bjoc.16.202

• with a length of 11.5 m and an inner diameter of 0.8 mm were wrapped around two Pyrex® glass columns. UV lamps were placed inside the glass columns. A representative setup is given in Figure 3a. The addition of isopropanol to 2(5H)-furanone in the presence of the photosensitizer 4,4’-dimethoxy

• light transmission through the 0.8 mm diameter microcapillary was around 65%. A higher DMBP concentration caused precipitations and resulted in a lower yield. Lower DMBP concentrations decreased the yield significantly, which decreased the PSTY values around 6-fold (data not shown). In another work, the

• ). This allowed for a larger reactor volume with the same illumination. The throughput was increased by using a larger volumetric flow rate. Several [3 + 2] photocycloadditions were performed. While scaling up, the concentration of the reactants, the diameter of the tubes, and the number of the reactors

Palladium nanoparticles supported on chitin-based nanomaterials as heterogeneous catalysts for the Heck coupling reaction

• Tony Jin,
• Malickah Hicks,
• Davis Kurdyla,
• Sabahudin Hrapovic,
• Edmond Lam and
• Audrey Moores

Beilstein J. Org. Chem. 2020, 16, 2477–2483, doi:10.3762/bjoc.16.201

• to the higher solubility of ChsNC. Both PdNP@ChNCs and PdNP@ChsNCs were imaged unstained to avoid any artefact in Pd imaging [19]. Dispersed “packets” of Pd NPs were observed for both samples, with far more packets observed for PdNP@ChNC (packet diameter of 42 ± 10 nm) samples compared to PdNP@ChsNC

• (packet diameter of 24 ± 7 nm) samples for the same wt/wt loading of the PdCl2 salt to ChNC/ChsNC (initially set to 1.6 wt %). It is also noted that the packets found in PdNP@ChsNC were almost half as small relative to PdNP@ChNC. At higher magnification, these packets are seen to be extremely small Pd NPs

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• (hydrodynamic diameter) of the nanoparticles in H2O was 198 ± 42 nm (Figure 4A, black). The measurements were performed also in phosphate-buffered saline (PBS) solution to evaluate a potential additional aggregation in cell medium. The aggregates were stable in solution and did not precipitate over time. The

• size of the nanoparticles dispersed in PBS was slightly larger compared to those in H2O, the hydrodynamic diameter was 246 ± 44 nm (Figure 4A, red). Moreover, TEM images (Figure 4B) showed that the nanoparticles of conjugate Dex-1b were quite polydisperse with a size comparable to the one obtained by

• S7 of Supporting Information File 1. ICP-AES boron content: 0.12 mg/g. Dex-1b A 10 mL stainless-steel mixing mill equipped with a 1 cm diameter ss ball was charged with 400 mg of 9–11 kDa dextran (at least 0.044 mmol), 17 mg of PBA-BODIPY (1, 0.044 mmol), and milled for 90 min at 25 Hz. The powder

Tools for generating and analyzing glycan microarray data

• Akul Y. Mehta,
• Jamie Heimburg-Molinaro and
• Richard D. Cummings

Beilstein J. Org. Chem. 2020, 16, 2260–2271, doi:10.3762/bjoc.16.187

• appropriate printing buffers depending upon the surface chemistry involved. A microarray printer, either contact-type or non-contact-type (e.g., piezoelectric dispensing), is used to dispense small drops of 50–100 μm in diameter each onto the slide surface in a rapid manner. Usually each sample is printed as

• pitch” (usually 2–4 times the diameter of the spots) to form distinct spots for analysis and to avoid merging of spots. Depending on the printer throughput, the number of slides/arrays to be printed and number of glycans to be printed, this process can take several hours or an entire day, and requires

Naphthalene diimide bis-guanidinio-carbonyl-pyrrole as a pH-switchable threading DNA intercalator

• Poulami Jana,
• Filip Šupljika,
• Carsten Schmuck and
• Ivo Piantanida

Beilstein J. Org. Chem. 2020, 16, 2201–2211, doi:10.3762/bjoc.16.185

• ct-DNA (Figure 6a) with a height of 2 nm (see Supporting Information File 1, Figure S26 for the height profile) and a length of a few micrometres, after the addition of compound 4 (r[4]/[DNA] = 0.1) formed disk-like aggregates with a diameter of 2 μm and a height of approximately 1 nm (Figure 6b

• higher r values (r = 1.25, excess of dye over DNA) more compact condensed DNA structures were observed with a diameter of 500 nm and a height of 10 nm (Figure 6c, see Supporting Information File 1, Figure S26 for height profile), so called polyplexes. For the estimation of the condensed particle size at

• more biologically relevant conditions (in aqueous solution) we used DLS. Pure ct-DNA gave rise to particles with an average diameter of 44 nm (Supporting Information File 1, Figure S25). The addition of compound 4 to the DNA led to the formation of condensed aggregates with a diameter increase of 60

Photosensitized direct C–H fluorination and trifluoromethylation in organic synthesis

• Shahboz Yakubov and
• Joshua P. Barham

Beilstein J. Org. Chem. 2020, 16, 2151–2192, doi:10.3762/bjoc.16.183

• through small-diameter (μm–mm) channels. Lectka and co-workers reported the processing of their benzil-photosensitized enone-directed C(sp3)–H fluorination in a custom-built flow reactor, comprised of a syringe pump, a coil of fluorinated ethylene propylene (FEP) tubing (7.5 m; inner diameter 1.6 mm

• ; outer diameter 3.2 mm; representing a 15 mL internal volume) and 6 × 20 W 72-LED work light sources (white LEDs, Scheme 30). The reaction mixture (a 12 mL slug) was pumped through. After 4 h, the coil was flushed through with MeCN to collect all of the reaction mixture. In the synthesis of 71, the flow

Design, synthesis and application of carbazole macrocycles in anion sensors

• Alo Rüütel,
• Ville Yrjänä,
• Sandip A. Kadam,
• Indrek Saar,
• Mihkel Ilisson,
• Astrid Darnell,
• Kristjan Haav,
• Tõiv Haljasorg,
• Lauri Toom,
• Johan Bobacka and
• Ivo Leito

Beilstein J. Org. Chem. 2020, 16, 1901–1914, doi:10.3762/bjoc.16.157

• , and 32 wt % PVC. A control membrane was also prepared with no ionophore, 0.7 wt % anion exchanger, 66 wt % DOS, and 33 wt % PVC. The dry weight of the membrane cocktails was 17% m/m. The sensors (Figure 2) were prepared with electrode bodies made from glassy carbon (GC) rods (diameter = 3 mm) encased

• in PVC cylinders (outer diameter = 8 mm). The GC rods functioned as the electronic conductors and the PVC shells were used to both control the amount of exposed GC surface and to function as the substrate for the ISM to adhere to. Poly(3,4-ethylenedioxythiophene) doped with chloride (PEDOT-Cl) was

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• wheat straw pulp led to 63% of isosorbide, corresponding to a productivity of 40 g·L−1·h−1 with 72% of purity. This high yield can be ascribed to several parameters such as small particle diameter, large surface area/porosity and lower crystallinity. For the particle size, cellulose fiber diameters are

Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers

• Alberto Rubin Pedrazzo,
• Fabrizio Caldera,
• Marco Zanetti,
• Silvia Lucia Appleton,
• Nilesh Kumar Dhakar and
• Francesco Trotta

Beilstein J. Org. Chem. 2020, 16, 1554–1563, doi:10.3762/bjoc.16.127

• carbonate NS synthesized in a solvent and displayed insolubility in water and organic solvents. FTIR and TG analyses were performed on the new material, confirming the structure with a carbonate bond. Nanoparticles, after cycles of ball milling and high-pressure homogenization had a mean diameter of less

• zirconium oxide balls of 10 mm diameter in 2 jars of 50 mL (10 balls per jar), also made from zirconium oxide. Rotation speed: sun wheel speed 600 rpm, changing rotation direction from clockwise to anticlockwise every 15 min. Thermogravimetric analyses were carried out on a Hi-res TGA 2050 Thermogravimetric

Heterogeneous photocatalysis in flow chemical reactors

• Christopher G. Thomson,
• Ai-Lan Lee and
• Filipe Vilela

Beilstein J. Org. Chem. 2020, 16, 1495–1549, doi:10.3762/bjoc.16.125

• of the photogenerated excitons is normally only a few nm3 and accounts for the large binding energy, as opposed to in a Si crystal, which has an exciton diameter in the order of 10s of nm3 [115]. Organic molecules will typically have large geometric relaxations to cope with the localised loss of

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• construction, pressure tolerance, heat conduction, and diameter/particle size matching; (3) the column orientation and setup–filters, etc.; (4) activation of the solid phase. The activation issue is one of the most important factors when considering the metal packing. Although our team had success with zinc

• keep the back pressure and a constant flow rate is achieved by the tubing length and diameter downstream of the pump or by the fluidic network for more complex cases. The flow is pulseless as a result of the fact that it is driven by compressed air. On-demand reagent (ODR) system design: The ODR

• . System setup: The internal diameter of the perfluorinated tubular reactor used on the ODR prototype was limited to 6.3 mm to maintain an efficient heat transfer. Due to this ID limitation and the heater dimensions, we decided to separate Mg and LiCl in two tubular reactors. First, the concentration

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• Instruments Q50 analyzer. The heating rate was 20 °C/min under nitrogen atmosphere. Cyclic voltammetry measurements were performed by using a glassy carbon working electrode (a disk with the diameter of 2 mm) in a three-electrode cell with an Autolab Type potentiostat–galvanostat. The measurements were

The charge-assisted hydrogen-bonded organic framework (CAHOF) self-assembled from the conjugated acid of tetrakis(4-aminophenyl)methane and 2,6-naphthalenedisulfonate as a new class of recyclable Brønsted acid catalysts

• Svetlana A. Kuznetsova,
• Alexander S. Gak,
• Yulia V. Nelyubina,
• Vladimir A. Larionov,
• Han Li,
• Michael North,
• Vladimir P. Zhereb,
• Alexander F. Smol'yakov,
• Artem O. Dmitrienko,
• Michael G. Medvedev,
• Igor S. Gerasimov,
• Ashot S. Saghyan and
• Yuri N. Belokon

Beilstein J. Org. Chem. 2020, 16, 1124–1134, doi:10.3762/bjoc.16.99

• of 15–30 μm. SEM imaging of crystals of F-1 in the F-1a phase formed from a DMSO/water system indicated the existence of two types of crystals (Figure 4). Type 1 was a set of platelets with heights of 0.7–1 mm, grown from a common planar base with a diameter of 0.1–0.3 mm. In other words, the

Synthesis of esters of diaminotruxillic bis-amino acids by Pd-mediated photocycloaddition of analogs of the Kaede protein chromophore

• Esteban P. Urriolabeitia,
• Pablo Sánchez,
• Alexandra Pop,
• Cristian Silvestru,
• Eduardo Laga,
• Ana I. Jiménez and
• Carlos Cativiela

Beilstein J. Org. Chem. 2020, 16, 1111–1123, doi:10.3762/bjoc.16.98

• 10 mm diameter each LED. The LEDs were serially connected in blocks of 6, with the minimum voltage possible (3 V) and a resistance of 60 Ω (according to Ohm's law). The output power per LED unit (blue, 465 nm) was 250 kmcd; the optical output power of the PCB of LEDs measured with a photometer

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• strain 3-44-a(19)T (AB302183). Fermentation Strain RD062863 growing on double-diluted ISP2 agar medium consisting of yeast extract 0.2%, malt extract 0.5%, glucose 0.2%, and agar 2% (pH 7.3) was inoculated into test tubes (inner diameter, 15 mm; length 16.5 cm) each containing 5 mL of YG seed medium

Visible-light-induced addition of carboxymethanide to styrene from monochloroacetic acid

• Kaj M. van Vliet,
• Nicole S. van Leeuwen,
• Albert M. Brouwer and
• Bas de Bruin

Beilstein J. Org. Chem. 2020, 16, 398–408, doi:10.3762/bjoc.16.38

• shell. We anticipated that in a flow setup using tubing with a small internal diameter (0.71 mm) the photocatalyzed reaction pathways could be more efficient. However, in this case, performing the reaction under flow conditions did not lead to better results. The reaction performed in a flow reactor led

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• with distilled water. Flowerpots with an inner diameter of 7.5 cm were filled with complex nutrient soil to three-fourths of their height. The above six weed targets were respectively grown in the pots and covered with soil to a thickness of 0.2 cm and grown in the greenhouse. When the weeds grew to

• , maize, cotton, soybean, and canola were selected to test the crop safety of compound II3, II4, and II5. The six crops were separately planted in flowerpots (12 cm diameter) containing the composite nutrient soil and grown at room temperature. When the crops had reached the four-leaf stage, the safety

Synthesis of 3-alkenylindoles through regioselective C–H alkenylation of indoles by a ruthenium nanocatalyst

• Abhijit Paul,
• Debnath Chatterjee,
• Srirupa Banerjee and
• Somnath Yadav

Beilstein J. Org. Chem. 2020, 16, 140–148, doi:10.3762/bjoc.16.16

• photolysis, was characterised by TEM (Figure S1, Supporting Information File 1), which showed polydispersed spherical particles of a size distribution mainly in the range of 10–25 nm, with a mean diameter of 15 nm. The size distribution of the particles from Figure S1, Supporting Information File 1, is

Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

• Sara Tejera,
• Giada Caniglia,
• Rosa L. Dorta,
• Andrea Favero,
• Javier González-Platas and
• Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

• prepared and characterized as described in reference [15]. Gelation test Melting points were measured using the dropping ball method. For that, a stainless steel ball of ca. 3 mm diameter (m = 130.2 mg) was placed on the gel in a tube with a diameter of 1 cm. This was placed inside an oil bath together

Plasma membrane imaging with a fluorescent benzothiadiazole derivative

• Pedro H. P. R. Carvalho,
• Jose R. Correa,
• Karen L. R. Paiva,
• Daniel F. S. Machado,
• Jackson D. Scholten and
• Brenno A. D. Neto

Beilstein J. Org. Chem. 2019, 15, 2644–2654, doi:10.3762/bjoc.15.257

• efficiently applied as selective plasma membrane probe in bioimaging experiments. Co-staining and PCC experiments confirmed the dye’s affinity for the plasma membrane and indicated its efficiency as a new bioprobe. Experimental NMR spectra were recorded on an NMR instrument using a 5 mm internal diameter

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

• as for [12 + H]+ (384.8 ± 0.41 Å2) and smaller than for the [12 + Na]+ complex, thus indicating inclusion complexation. This clearly indicates that the Me4N+ complex of 12 has the same rotation average diameter as the protonated dimer and thus the cation is encapsulated inside the cavity. Calculated

Targeted photoswitchable imaging of intracellular glutathione by a photochromic glycosheet sensor

• Xianzhi Chai,
• Hai-Hao Han,
• Yi Zang,
• Jia Li,
• Xiao-Peng He,
• Junji Zhang and
• He Tian

Beilstein J. Org. Chem. 2019, 15, 2380–2389, doi:10.3762/bjoc.15.230

• obvious morphology of nanosheets which presented a large 2D and ultrathin plane with a diameter of ca. 200 nm (Figure 2B) [33][34]. By virtue of the expansive surface, 2D MnO2 nanosheets possess the ability to load dozens of fluorophores. An array of fluorescent reporters thus formed, which facilitate

Small anion-assisted electrochemical potential splitting in a new series of bistriarylamine derivatives: organic mixed valency across a urea bridge and zwitterionization

• Keishiro Tahara,
• Tetsufumi Nakakita,
• Alyona A. Starikova,
• Takashi Ikeda,
• Masaaki Abe and
• Jun-ichi Kikuchi

Beilstein J. Org. Chem. 2019, 15, 2277–2286, doi:10.3762/bjoc.15.220

• . Electrochemical investigations The electrochemical behavior was investigated using a BAS electrochemical analyzer (Bioanalytical Systems Inc, West Lafayette, IN, USA) with a three-electrode system composed of a platinum wire (1.6 mm diameter) counter electrode, a glassy carbon working electrode (3.0 mm diameter