Beilstein Journal of Organic Chemistry Beilstein Journal of Organic Chemistry RSS feedThis is an RSS file. You can use it to subscribe to this data in your favourite RSS reader or to display this data on your own website or blog.

Biphenylene-containing polycyclic conjugated compounds
Abstract There has been a growing emphasis on the synthesis of polycyclic conjugated compounds, driven by their distinct structural characteristics that make them valuable candidates for use in cutting-edge technologies. In particular, acenes, a subgroup of polycyclic aromatic compounds, are sought-after synthetic targets due to their remarkable optoelectronic properties which stem from their π-conjugation and planar structure. Despite all these promising characteristics, acenes exhibit significant stability problems when their conjugation enhances. Various approaches have been developed to address this stability conc...
Source: Beilstein Journal of Organic Chemistry - December 13, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acenes biphenylene [N]phenylenes polycyclic aromatic compounds Review Source Type: research

Aromatic systems with two and three pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile fragments as electron-transporting organic semiconductors exhibiting long-lived emissions
This study focuses on the synthesis and investigation of the semiconducting properties of polyaromatic π-systems containing two and three fragments of pyridine-2,6-dicarbazolyl-3,5-dicarbonitrile. The compounds are synthesized by Sonogashira coupling reactions and characterized by steady-state and time-resolved luminescence spectroscopy. The compounds show efficient intramolecular charge transfer (ICT) from the donor to the acceptor. The photoluminescence (PL) spectra of the solutions of the compounds showed non-structured emission peaks in the visible region, which are attributed to ICT emission. The PL intensities o...
Source: Beilstein Journal of Organic Chemistry - December 12, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: charge transport intramolecular charge transfer photophysical properties pyridine-3,5-dicarbonitrile Full Research Paper Source Type: research

Anion – π catalysis on carbon allotropes
Abstract Anion–π catalysis, introduced in 2013, stands for the stabilization of anionic transition states on π-acidic aromatic surfaces. Anion–π catalysis on carbon allotropes is particularly attractive because high polarizability promises access to really strong anion–π interactions. With these expectations, anion–π catalysis on fullerenes has been introduced in 2017, followed by carbon nanotubes in 2019. Consistent with expectations from theory, anion–π catalysis on carbon allotropes generally increases with polarizability. Realized examples reach from enolate a...
Source: Beilstein Journal of Organic Chemistry - December 12, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: anion – π interactions autocatalysis carbon nanotubes Diels Alder reactions electric-field-induced catalysis electromicrofluidics enolate addition ether cyclizations fullerenes Review Source Type: research

Controlling the reactivity of La@C82 by reduction: reaction of the La@C82 anion with alkyl halide with high regioselectivity
In this study, the thermal reaction of the La@C2v-C82 anion with benzyl bromide derivatives 1 at 110 °C afforded single-bonded adducts 2–5 with high regioselectivity. The products were characterized by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry and visible–near infrared spectroscopy. The reaction of La@C2v-C82 with alkyl halides using the same conditions showed no consumption of La@C2v-C82, indicating that the reactivity of La@C2v-C82 toward alkyl halides was effectively increased by one-electron reduction. Single-crystal X-ray diffraction analysis of the single-bonded add...
Source: Beilstein Journal of Organic Chemistry - December 11, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: electron transfer metallofullerene radical reduction Full Research Paper Source Type: research

N-Boc- α -diazo glutarimide as efficient reagent for assembling N-heterocycle-glutarimide diads via Rh(II)-catalyzed N – H insertion reaction
Abstract A technique has been proposed for incorporating a heterocyclic component into a glutarimide framework employing a Rh2(esp)2-catalyzed N–H insertion with the involvement of N-Boc-α-diazo glutarimide. The new diazo reagent is more stable, soluble and convenient to prepare than the previously suggested one. The approach permits the application of diverse heterocycles, including both aromatic and saturated NH-substrates. This yields structures that are appealing for generating cereblon ubiquitin-ligase ligands and for potential use in crafting PROTAC molecules. Beilstein J. Org. Chem. 2023, 19, 1841–...
Source: Beilstein Journal of Organic Chemistry - December 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: CRBN ligands diazocarbonyl compounds – H insertion reaction N-heterocycles Rh(II)-catalysis Full Research Paper Source Type: research

Thienothiophene-based organic light-emitting diode: synthesis, photophysical properties and application
Abstract A donor–π–acceptor (D–π–A)-type pull–push compound, DMB-TT-TPA (8), comprising triphenylamine as donor and dimesitylboron as acceptor linked through a thieno[3,2-b]thiophene (TT) π-conjugated linker bearing a 4-MeOPh group, was designed, synthesized, and fabricated as an emitter via a solution process for an organic light-emitting diode (OLED) application. DMB-TT-TPA (8) exhibited absorption and emission maxima of 411 and 520 nm, respectively, with a mega Stokes shift of 109 nm and fluorescence quantum yields both in the solid state (41%) and in solution (86%). The opti...
Source: Beilstein Journal of Organic Chemistry - December 7, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: OLED organoboron solution processes thienothiophene triphenylamine Full Research Paper Source Type: research

Substituent-controlled construction of A4B2-hexaphyrins and A3B-porphyrins: a mechanistic evaluation
Abstract A substituent-dependent construction of novel A3B-porphyrins along with A4B2-hexaphyrins was realized by the reactions of N-tosylimines and meso-aryl-substituted tripyrranes in the presence of Cu(OTf)2 as the catalyst. The reaction mechanism of the presented method was studied on model reactions by electrospray-ionization time-of-flight (HRESI–TOF) mass spectral analysis in a timely manner. The analytical results indicated that the observed azafulvene-ended di- and tripyrrolic intermediates are responsible for the formation of porphyrinogen and hexaphyrinogen forms. Beilstein J. Org. Chem. 2023, 19, 1832...
Source: Beilstein Journal of Organic Chemistry - December 6, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: A4B2-hexaphyrin A3B-porphyrin N-tosylimine Cu(OTf)2 catalysis HRESI – TOF analysis Full Research Paper Source Type: research

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data
In this study, we used a Bayesian deep neural network model to automatically identify and classify vibrational fingerprints of several monosaccharides. We report high performances of the obtained trained algorithm (GlAIcomics), that can be used to discriminate contamination and identify a molecule with a high degree of confidence. It opens the possibility to use artificial intelligence in combination with spectroscopy-augmented mass spectrometry for carbohydrates sequencing and glycomics applications. Beilstein J. Org. Chem. 2023, 19, 1825–1831. doi:10.3762/bjoc.19.134 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - December 5, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: Bayesian neural network deep learning glycomics IR spectroscopy Full Research Paper Source Type: research

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen
Abstract Synthesizing organocatalysts is often a long and cost-intensive process, therefore, the recovery and reuse of the catalysts are particularly important to establish sustainable organocatalytic transformations. In this work, we demonstrate the synthesis, application, and recycling of a new lipophilic cinchona squaramide organocatalyst. The synthesized lipophilic organocatalyst was applied in Michael additions. The catalyst was utilized to promote the Michael addition of cyclohexyl Meldrum’s acid to 4-chloro-trans-β-nitrostyrene (quantitative yield, up to 96% ee). Moreover, 1 mol % of the catalyst was feas...
Source: Beilstein Journal of Organic Chemistry - November 24, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: baclofen catalyst recovery lipophilic cinchona squaramide organocatalysis stereoselective catalysis Full Research Paper Source Type: research

Synthetic approach to 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides based on common β -keto amide precursors
Abstract β-Keto amides were used as convenient precursors to both 2-alkyl-4-quinolones and 2-alkyl-4-quinolone-3-carboxamides. The utility of this approach is demonstrated with the synthesis of fourteen novel and four known quinolone derivatives, including natural products of microbial origin such as HHQ and its C5-congener. Two compounds with high activity against S. aureus have been identified among the newly obtained quinolones, with MICs ≤ 3.12 and ≤ 6.25 µg/mL, respectively. Beilstein J. Org. Chem. 2023, 19, 1804–1810. doi:10.3762/bjoc.19.132 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - November 23, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: antibacterial β -keto amides enaminones 4-quinolones quorum sensing Full Research Paper Source Type: research

Recent advancements in iodide/phosphine-mediated photoredox radical reactions
Abstract Photoredox catalysis plays a crucial role in contemporary synthetic organic chemistry. Since the groundbreaking work of Shang and Fu on photocatalytic decarboxylative alkylations in 2019, a wide range of organic transformations, such as alkylation, alkenylation, cyclization, amination, iodination, and monofluoromethylation, have been progressively achieved using a combination of iodide and PPh3. In this review, we primarily focus on summarizing the recent advancements in inexpensive and readily available iodide/phosphine-mediated photoredox radical transformations. Beilstein J. Org. Chem. 2023, 19, 1785–180...
Source: Beilstein Journal of Organic Chemistry - November 22, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: annulation decarboxylative iodide/phosphine photocatalytic radical reaction Review Source Type: research

Active-metal template clipping synthesis of novel [2]rotaxanes
We present herein a new synthetic strategy to access [2]rotaxanes, namely active-metal template clipping. We discuss the design of the target [2]rotaxanes, synthesis and characterization of the axle, macrocycle precursors and macrocycles as well as preparation of the final [2]rotaxanes by active template copper(I)-catalyzed alkyne–azide cycloaddition (CuAAC) as key step of the synthesis. HRMS and NMR experiments have been performed to confirm the formation of the interlocked structures. Beilstein J. Org. Chem. 2023, 19, 1776–1784. doi:10.3762/bjoc.19.130 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - November 20, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: active-metal template clipping copper(I)-catalyzed alkyne – azide cycloaddition mechanically interlocked structures [2]rotaxanes Full Research Paper Source Type: research

Selectivity control towards CO versus H2 for photo-driven CO2 reduction with a novel Co(II) catalyst
Abstract Developing efficient catalysts for reducing carbon dioxide, a highly stable combustion waste product, is a relevant task to lower the atmospheric concentration of this greenhouse gas by upcycling. Selectivity towards CO2-reduction products is highly desirable, although it can be challenging to achieve since the metal-hydrides formation is sometimes favored and leads to H2 evolution. In this work, we designed a cobalt-based catalyst, and we present herein its physicochemical properties. Moreover, we tailored a fully earth-abundant photocatalytic system to achieve specifically CO2 reduction, optimizing efficiency an...
Source: Beilstein Journal of Organic Chemistry - November 17, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: carbon monoxide selectivity cobalt(II) complex copper(I) complex earth-abundant hexafluoropropanol photocatalytic CO2 reduction Full Research Paper Source Type: research

Charge carrier transport in perylene-based and pyrene-based columnar liquid crystals
Abstract Electron and hole transport characteristics were evaluated for perylene-based and pyrene-based compounds using electron-only and hole-only devices. The perylene presented a columnar hexagonal liquid crystal phase at room temperature with strong molecular π-stacking inside the columns. The pyrene crystallizes bellow 166 °C, preserving the close-packed columnar rectangular structure of the mesophase. Photophysical analysis and numerical calculations assisted the interpretation of positive and negative charge carrier mobilities obtained from fitting the space charge limited regime of current vs voltage curv...
Source: Beilstein Journal of Organic Chemistry - November 16, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: charge carrier transport columnar liquid crystal organic electronics perylene pyrene Full Research Paper Source Type: research

Trifluoromethylated hydrazones and acylhydrazones as potent nitrogen-containing fluorinated building blocks
Abstract Nitrogen-containing organofluorine derivatives, which are prepared using fluorinated building blocks, are among the most important active fragments in various pharmaceutical and agrochemical products. This review focuses on the reactivity, synthesis, and applications of fluoromethylated hydrazones and acylhydrazones. It summarizes recent methodologies that have been used for the synthesis of various nitrogen-containing organofluorine compounds. Beilstein J. Org. Chem. 2023, 19, 1741–1754. doi:10.3762/bjoc.19.127 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - November 15, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: acylhydrazones difluoromethylation dihydropyridazine fluorinated building blocks imidazolidines pyrazoles pyrazolidines pyrazolines trifluoromethylation Review Source Type: research