Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• ” was next tested at the device fabrication stage in the case of OFETs. An Al2O3/SiO2 dielectric layer with a self-assembled monolayer of 12-cyclohexyldodecylphosphonic acid was chosen as substrate and thin-films of sulfoxide 4a were formed by spin-coating from a chloroform solution. After thermal

Quinoxaline derivatives as attractive electron-transporting materials

• Zeeshan Abid,
• Liaqat Ali,
• Sughra Gulzar,
• Faiza Wahad,
• Raja Shahid Ashraf and
• Christian B. Nielsen

Beilstein J. Org. Chem. 2023, 19, 1694–1712, doi:10.3762/bjoc.19.124

• self-assembled monolayer in devices. The molecular dipole and work function of gold was adjusted by using fluorine and CN as well as dimethylamino substituents on the quinoxaline. Notably, the researchers tuned the work function of gold over a range of 1.0 eV [59]. The study by You et al. quoted in the

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• chiral nanographenes. Keywords: chiral nanographene; helicene; racemization barrier; Scholl reaction; single-crystal X-ray diffractometry; Introduction Graphene, an allotrope of carbon, has captured widespread attention since it was first experimentally demonstrated as a monolayer of carbon atoms [1

Insight into oral amphiphilic cyclodextrin nanoparticles for colorectal cancer: comprehensive mathematical model of drug release kinetic studies and antitumoral efficacy in 3D spheroid colon tumors

• Sedat Ünal,
• Gamze Varan,
• Juan M. Benito,
• Yeşim Aktaş and
• Erem Bilensoy

Beilstein J. Org. Chem. 2023, 19, 139–157, doi:10.3762/bjoc.19.14

• reported that depletion of cholesterol by methyl-β-cyclodextrin could inhibit EGFR signals, induce apoptosis, and suppress tumor growth in colon tumor-induced mice [57]. Shimolina et al. evaluated membrane fluidity in CT26 and HeLa Kyoto cells treated with cisplatin in a monolayer conventional cell culture

• enhanced as a result of the formulation's exposure to cells arranged in a monolayer. However, in a 3D cell culture, the disparity in cell proliferation values in mouse and human cell lines is smaller (Figure 8). In terms of formulations, only the 6-O-capro-β-CD nanoparticles have more significant effect on

• CT26 cells, whilst no other nanoparticle groups show this variation between cell lines. In 2D conventional cell culture, the cells form a monolayer on the plate and all cells interact equally and directly with the added drug or nanoparticle formulation. Furthermore, it is well recognized that increased

Microelectrode arrays, electrosynthesis, and the optimization of signaling on an inert, stable surface

• Kendra Drayton-White,
• Siyue Liu,
• Yu-Chia Chang,
• Sakashi Uppal and
• Kevin D. Moeller

Beilstein J. Org. Chem. 2022, 18, 1488–1498, doi:10.3762/bjoc.18.156

• of the molecules placed at those sites. In the majority of such studies, the molecules to be added to the electrodes in an array are attached directly to the array either through the use of a self-assembled monolayer or direct functionalization of a carbon electrode [12][13]. Following the synthetic

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• II [75] was cross-linked by bis-nitrilotriacetic acid yielding fibrous cellulose [76]. Cross-linked enzymes are believed to arrange their catalytic core domains and promote the formation of cellulose with high crystallinity. A similar principle was also demonstrated on a self-assembled monolayer [77

Chemical approaches to discover the full potential of peptide nucleic acids in biomedical applications

• Nikita Brodyagin,
• Martins Katkevics,
• Venubabu Kotikam,
• Christopher A. Ryan and
• Eriks Rozners

Beilstein J. Org. Chem. 2021, 17, 1641–1688, doi:10.3762/bjoc.17.116

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

• Premansh Dudhe,
• Mena Asha Krishnan,
• Kratika Yadav,
• Diptendu Roy,
• Krishnan Venkatasubbaiah,
• Biswarup Pathak and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101

• (4,200 cells/well) and allowed to form a monolayer for a period of 48 h. Old medium was replaced with fresh medium (0.2 mL) containing an increasing concentration of γ-carboline derivatives 3ac, 3bc, 3ca, 3ga and doxorubicin (0.1 μM, 0.25 μM, 0.5 μM, 1 μM, 2.5 μM, 5 μM, 10 μM, 25 μM, 50 μM, 100 μM) and

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

• Masayori Hagimori,
• Estefanía E. Mendoza-Ortega and
• Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

• . By contrast, the hydrocarbon lipopeptide led to microbubbles with a larger mean diameter and a significantly lower stability. Keywords: adsorption at fluid interfaces; drug delivery; microbubble targeting; molecular imaging; monolayer; perfluoroalkylated lipopeptide; solid-phase peptide synthesis

• ability to self-assemble into spontaneously adsorbed monolayers at the air/water interface and also to adsorb on a DPPC monolayer spread at the air/water interface. Finally, the size and stability characteristics of perfluorohexane (F-hexane)-stabilized microbubbles with DPPC/DPPE-PEG2000 shells and

• that of the hydrocarbon compound (characteristic time of adsorption τ ≈ 0.5 min for 1–3 versus ≈2.5 min for 4). Adsorption of lipid–peptide conjugates on a phospholipid monolayer spread at the air/water interface. DPPC is widely used in the formulation of liposomes and microbubbles [31][33]. In order

Control over size, shape, and photonics of self-assembled organic nanocrystals

• Chen Shahar,
• Yaron Tidhar,
• Yunmin Jung,
• Haim Weissman,
• Sidney R. Cohen,
• Ronit Bitton,
• Iddo Pinkas,
• Gilad Haran and
• Boris Rybtchinski

Beilstein J. Org. Chem. 2021, 17, 42–51, doi:10.3762/bjoc.17.5

• monolayer surface so that it does not allow facile bulk fabrication and restricts control over the crystal morphology [22][23]. Crystalline nanobelts assembled from perylene and perylene diimide (PDI) derivatives were reported, but their size and shape could not be controlled [24][25]. Modification of the

• PDI system with a hydrophilic group (phenoxybenzoic acid) attached to the aromatic core of PDI at the “bay area” [35]. Compound 1 is an asymmetric amphiphile that was designed to result in arrays that differ from fibrous and monolayer structures assembled from symmetrically substituted PDI systems [36

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• preferred binding mode of zinc(II)–dipicolylamine complexes with phosphate anions which involves binding of the anion between two metal centers. This work thus provided information on how the behavior of mixed monolayer-protected gold nanoparticles is affected by multivalent interactions, at the same time

• binding of these anions to the immobilized receptor units strengthened their interaction with a simultaneously present bis(imidazolium) ion, which in turn caused nanoparticle crosslinking [16][17]. Our group recently showed that a mixed monolayer-protected AuNP containing solubilizing triethylene glycol

• that the anion binding must involve more than one receptor unit to induce nanoparticle crosslinking (Figure 1). The use of mixed monolayer-protected AuNPs moreover allows varying the ratio of the ligands on the nanoparticle surface, of which one is responsible for the analyte recognition, while the

An improved, scalable synthesis of Notum inhibitor LP-922056 using 1-chloro-1,2-benziodoxol-3-one as a superior electrophilic chlorinating agent

• Nicky J. Willis,
• Elliott D. Bayle,
• George Papageorgiou,
• David Steadman,
• Benjamin N. Atkinson,
• William Mahy and
• Paul V. Fish

Beilstein J. Org. Chem. 2019, 15, 2790–2797, doi:10.3762/bjoc.15.271

• these specific amides demonstrated the required combination of sufficient MLM stability along with cell permeability as measured by transit performance across a MDCK-MDR1 monolayer without evidence of P-gp mediated efflux. This collection of data for amides 17a–r is shared as ‘open data’ to assist

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• Hydrolysis of ʟ-Leu-AMC by the surface-bound aminopeptidases of KB3.1 cells was assayed based on the method from Weber and co-workers [6] with slight modifications. KB3.1 cells were grown as monolayer cultures in Dulbecco's modified Eagle's medium (DMEM) containing 10% fetal calf serum at 37 °C in 24-well

Nanopatterns of arylene–alkynylene squares on graphite: self-sorting and intercalation

• Tristan J. Keller,
• Joshua Bahr,
• Kristin Gratzfeld,
• Nina Schönfelder,
• Marcin A. Majewski,
• Marcin Stępień,
• Sigurd Höger and
• Stefan-S. Jester

Beilstein J. Org. Chem. 2019, 15, 1848–1855, doi:10.3762/bjoc.15.180

• in the monolayer. The changes in the supramolecular lattice are accompanied by subtle changes of the backbone geometries, i.e., an increase of the interior angle α◊ to (87 ± 4)° in 1b (as compared to (80 ± 4)° in 1a). The changes of the backbone shape together with the partly hexyloxy-filled interior

• -)assembled from a 5 × 10−7 M solution of 1a to HOPG (at an elevated temperature, 80 °C), and (after cooling of the sample to rt) a 1 × 10−6 M solution of 2 in TCB was added. By STM (Figure 3a), a monolayer of 1a (polymorph A) is observed (and expected in that concentration range, cf. Figure 2a). However

• and e have the same orientation as the hexagons in the underlying graphene layer, and therefore the same orientation as proposed in the self-assembled monolayer of pure 2 (see Supporting Information File 1), and other large PAHs on HOPG [36]. However, 2 in Figure 3b and d is rotated by 30°. This is

Norbornadiene-functionalized triazatriangulenium and trioxatriangulenium platforms

• Roland Löw,
• Talina Rusch,
• Tobias Moje,
• Fynn Röhricht,
• Olaf M. Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1815–1821, doi:10.3762/bjoc.15.175

• temperature (Figure 5a). The molecules form a hexagonally ordered self-assembled monolayer (SAM) with an intermolecular distance of (1.23 ± 0.07) nm. This is in agreement with a (√19 × √19) R23.4° superstructure, which was observed in our previous investigations of adlayers of octyl-TATA derivatives [1][6][19

• would have to be in the switched state 1b. The second explanation, i.e., that the mixed monolayer consists of octyl-TATA 6 and the NBD-TATA 1a, seems to be more likely, since molecule 1 decays slowly under irradiation in contact with oxygen. Previous measurements have shown that self-assembly from

Diazocine-functionalized TATA platforms

• Roland Löw,
• Talina Rusch,
• Fynn Röhricht,
• Olaf Magnussen and
• Rainer Herges

Beilstein J. Org. Chem. 2019, 15, 1485–1490, doi:10.3762/bjoc.15.150

• ” (triazatriangulenium) platforms which adsorb on Au(111) surfaces. A spacer, such as an ethynyl group is connected to the central carbon atom like a post and the azobenzene is mounted on top of the spacer. After preparation of an ordered self-assembled monolayer on gold, the azobenzene units are freestanding upright on

Fabrication, characterization and adsorption properties of cucurbit[7]uril-functionalized polycaprolactone electrospun nanofibrous membranes

• Changzhong Chen,
• Fengbo Liu,
• Xiongzhi Zhang,
• Zhiyong Zhao and
• Simin Liu

Beilstein J. Org. Chem. 2019, 15, 992–999, doi:10.3762/bjoc.15.97

• place at specific homogeneous sites within the nanofibrous membrane and formed a monolayer coverage of MB at the surface of the nanofibrous membrane [34]. The morphology of PCL and PCL/CB[7] nanofibers after the absorption experiment are shown in Figure S9 (Supporting Information File 1). It is found

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

Novel solid-phase strategy for the synthesis of ligand-targeted fluorescent-labelled chelating peptide conjugates as a theranostic tool for cancer

• Sagnik Sengupta,
• Mena Asha Krishnan,
• Premansh Dudhe,
• Ramesh B. Reddy,
• Bishnubasu Giri,
• Sudeshna Chattopadhyay and
• Venkatesh Chelvam

Beilstein J. Org. Chem. 2018, 14, 2665–2679, doi:10.3762/bjoc.14.244

• conjugates 13 or 17. Culture of human cancer and epithelial cell lines: LNCaP and CHO-β cells were obtained as gift from Prof. Philip S. Low, Purdue University, West Lafayette, USA whereas the PC-3 cell line was purchased from NCCS, Pune, India. LNCaP cells were grown as a monolayer using 1640 RPMI medium

Synergistic electrodeposition of bilayer films and analysis by Raman spectroscopy

• Saadeldin E. T. Elmasly,
• Luca Guerrini,
• Joseph Cameron,
• Alexander L. Kanibolotsky,
• Neil J. Findlay,
• Karen Faulds and
• Peter J. Skabara

Beilstein J. Org. Chem. 2018, 14, 2186–2189, doi:10.3762/bjoc.14.191

• for the fabrication of complex, multilayer organic electronic devices. Oxidative wave for PEDOT (black line) and PEDTT (dashed line), together with the corresponding structures. Normalised Raman spectra of (a) doped PEDOT monolayer; (b) de-doped PEDOT monolayer; (c) doped PEDTT monolayer; (d) de-doped

• PEDTT monolayer; (e) doped PEDOT/PEDTT bilayer; (f) de-doped PEDOT/PEDTT bilayer. Supporting Information Supporting Information File 204: General experimental and additional spectra. Acknowledgements PJS thanks the Royal Society for a Wolfson Research Merit Award. NJF, JC and AK thank the EPSRC for

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• crossbar architecture in which a monolayer of amphiphilic rotaxanes is sandwiched by a bottom Si nanowire electrode and a top Ti nanowire electrode. Both layers of nanowires are orthogonal to each other. This produces several crossing points or “junctions” whose areas are defined by the diameter of the

• “molecular muscles” can accumulate their force and consequently deform a material by concerted switching. In rotaxane 21, the two macrocycles are attached by disulfide anchors to the gold surface of microcantilever beams (500 × 100 × 1 µm) and form a self-assembled monolayer. Chemical oxidation leads to a

Mechanochemistry of nucleosides, nucleotides and related materials

• Olga Eguaogie,
• Joseph S. Vyle,
• Patrick F. Conlon,
• Manuela A. Gîlea and
• Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

• Pluronic F68®) were prepared in a mixer ball mill over three hours [88]. All dispersions displayed antiviral activity and enhanced aqueous dissolution rates. The Pluoronic F68® dispersion displayed enhanced transport rates across a model intestinal cell monolayer. The conversion of a stable ribavirin

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

• Vivek Poonthiyil,
• Thisbe K. Lindhorst,
• Vladimir B. Golovko and
• Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

• synthesized in two steps (Scheme 5). Herein, the treatment of methyl-terminated triethylene glycol monolayer-protected AuNPs (Me-EG3-AuNPs) with ω-carboxy tetraethylene glycol thiols (HOOC-EG4-SH) gave carboxy-functionalized AuNPs (HOOC-EG4-AuNPs). Peptide coupling of these HOOC-EG4-AuNPs with a DBCO-amine

A recursive microfluidic platform to explore the emergence of chemical evolution

• David Doran,
• Marc Rodriguez-Garcia,
• Rebecca Turk-MacLeod,
• Geoffrey J. T. Cooper and
• Leroy Cronin

Beilstein J. Org. Chem. 2017, 13, 1702–1709, doi:10.3762/bjoc.13.164

• valves are necessary. The incubation chamber (Figure 7d) represents a means of visualising a monolayer of droplets over time, which could be useful if we are looking to monitor the droplet coarsening process over time. However, this module could be replaced by a delay line or an off-chip incubation

Sugar-based micro/mesoporous hypercross-linked polymers with in situ embedded silver nanoparticles for catalytic reduction

• Qing Yin,
• Qi Chen,
• Li-Can Lu and
• Bao-Hang Han

Beilstein J. Org. Chem. 2017, 13, 1212–1221, doi:10.3762/bjoc.13.120

• SugPOP-2 displays a type I sorption isotherm. A rapid uptake curve reflects the microporous monolayer adsorption tendency at low relative pressure (p/p0 < 0.10). As for SugPOP-1 and SugPOP-3, the significant hysteresis loops (0.50 < p/p0 < 1.00) are consistent with the mesoporous structure. The SSA value