Beilstein Journal of Organic Chemistry This 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.

Unprecedented synthesis of a 14-membered hexaazamacrocycle
Abstract The transformation of 3-[(ethoxymethylene)amino]-1-methyl-1H-pyrazole-4-carbonitrile into the 14-membered macrocycle, 2,10-dimethyl-2,8,10,16-tetrahydrodipyrazolo[3,4-e:3',4'-l][1,2,4,8,9,11]hexaazacyclotetradecine-4,12-diamine, by the reaction with excess hydrazine under various conditions was studied in detail. The reaction proceeded through the initial formation of 4-imino-2-methyl-2,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine followed by dimerization to give the final macrocycle. A convenient synthesis of the latter starting from 4-imino-2-methyl-2,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-amine was de...
Source: Beilstein Journal of Organic Chemistry - November 15, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: amidrazones hexaazamacrocycles pyrazolo[3,4-d]pyrimidines ring contraction self-assembly Full Research Paper Source Type: research

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups
In this study, two new structure-related 3,4,5-trimethoxybenzoyl-containing N-acylhydrazones were synthesized and fully characterized, both in solution and in the solid state. The compounds differ with respect to the carbonyl precursors, i.e., 3-substituted salicylaldehydes with either a methyl or a nitro group. Single crystals of both compounds were isolated from the respective mother liquors and, in both cases, XRD confirmed the obtention of the (E)-isomer, in an anti-conformation. Computational calculations (gas and water phases) were performed in order to confirm some of the structural and vibrational aspects of the co...
Source: Beilstein Journal of Organic Chemistry - November 10, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: DFT calculations N-acylhydrazones phenol acidity ring substituents XRD Full Research Paper Source Type: research

Quinoxaline derivatives as attractive electron-transporting materials
Abstract This review article provides a comprehensive overview of recent advancements in electron transport materials derived from quinoxaline, along with their applications in various electronic devices. We focus on their utilization in organic solar cells (OSCs), dye-sensitized solar cells (DSSCs), organic field-effect transistors (OFETs), organic-light emitting diodes (OLEDs) and other organic electronic technologies. Notably, the potential of quinoxaline derivatives as non-fullerene acceptors in OSCs, auxiliary acceptors and bridging materials in DSSCs, and n-type semiconductors in transistor devices is discussed in de...
Source: Beilstein Journal of Organic Chemistry - November 9, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: electron transport materials non-fullerene acceptors n-type semiconductors organic electronics quinoxalines Review Source Type: research

Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds
This article highlights our recent work on the development of α-amino acid-based [3 + 2] cycloaddition reactions of N–H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products. Beilstein J. Org. Chem. 2023, 19, 1677–1693. doi:10.3762/bjoc.19.123 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - November 6, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: [3 2] cycloaddition decarboxylation 1,3-dipolar double cycloaddition one-pot synthesis multicomponent reaction semi-stabilized azomethine ylide Perspective Source Type: research

A deep-red fluorophore based on naphthothiadiazole as emitter with hybridized local and charge transfer and ambipolar transporting properties for electroluminescent devices
Abstract Herein, we report the synthesis and characterization of an efficient ambipolar charge-carrier-transporting deep-red fluorophore (TPECNz) based on a donor–acceptor–donor (D–A–D)-type molecule and its application as a non-doped emitter in an organic light-emitting diode (OLED). The fluorophore TPECNz contains naphtho[2,3-c][1,2,5]thiadiazole (Nz) as a strong acceptor unit symmetrically functionalized with N-(4-(1,2,2-triphenylvinyl)phenyl)carbazole as a donor and aggregation-induced emission (AIE) luminogen. The experimental (solvatochromic and emission in THF/water mixtures studies) and theo...
Source: Beilstein Journal of Organic Chemistry - November 3, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: ambipolar material deep red fluorophore hybridized local and charge transfer naphthothiadiazole OLED organic light-emitting diode Full Research Paper Source Type: research

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity
Abstract 1,3-Dimethyl-2,3-dihydrobenzo[d]imidazoles, 1H, and 1,1',3,3'-tetramethyl-2,2',3,3'-tetrahydro-2,2'-bibenzo[d]imidazoles, 12, are of interest as n-dopants for organic electron-transport materials. Salts of 2-(4-(dimethylamino)phenyl)-4,7-dimethoxy-, 2-cyclohexyl-4,7-dimethoxy-, and 2-(5-(dimethylamino)thiophen-2-yl)benzo[d]imidazolium (1g–i+, respectively) have been synthesized and reduced with NaBH4 to 1gH, 1hH, and 1iH, and with Na:Hg to 1g2 and 1h2. Their electrochemistry and reactivity were compared to those derived from 2-(4-(dimethylamino)phenyl)- (1b+) and 2-cyclohexylbenzo[d]imida...
Source: Beilstein Journal of Organic Chemistry - November 1, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: benzoimidazole crystal structure kinetics n-dopant reduction Full Research Paper Source Type: research

Tying a knot between crown ethers and porphyrins
Abstract Porphyrins and crown ether hybrids have emerged as a promising class of molecules composed of elements of a tetrapyrrole macrocycle and an oligo(ethylene glycol) segment. These hybrid systems constitute a broad group of compounds, including crowned porphyrins, crownphyrins, and calixpyrrole-crown ether systems forming Pacman complexes with transition metals. Their unique nature accustoms them as excellent ligands and hosts capable of binding guest molecules/ions, but also to undergo unusual transformations, such as metal-induced expansion/contraction. Depending on the design of the particular hybrid, they present ...
Source: Beilstein Journal of Organic Chemistry - October 27, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: crown ethers porphyrinoids self-assembly sensors supramolecular chemistry Perspective Source Type: research

A series of perylene diimide cathode interlayer materials for green solvent processing in conventional organic photovoltaics
Abstract Herein, we report on the design, synthesis, physical and chemical properties, and organic photovoltaic (OPV) device performance of four new cathode interlayer (CIL) materials based on bay N-annulated perylene diimides. Starting from the previously reported N-annulated perylene diimide (PDIN-H), the N-position was functionalized with a benzyl and pentafluorobenzyl group to make PDIN-B and PDIN-FB, respectively. Similarly, starting from the previously reported cyanated N-annulated perylene diimide (CN-PDIN-H), the N-position was functionalized with a benzyl and pentafluorobenzyl group to make CN-PDIN-B and CN-PDIN-F...
Source: Beilstein Journal of Organic Chemistry - October 26, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cathode interlayer materials green solvent processing organic photovoltaics Full Research Paper Source Type: research

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions
Abstract The 7-azabicyclo[4.3.1]decane ring system, common to a number of biologically active alkaloids, was accessed from tropone (via its η4-diene complex with Fe(CO)3) in a short sequence of steps: 1) nucleophilic amine addition and subsequent Boc-protection, 2) photochemical demetallation of the iron complex, and 3) an intramolecular Heck reaction. Minor modifications to the protocol enabled access to the related 2-azabicyclo[4.4.1]undecane system, albeit in lower yield. Beilstein J. Org. Chem. 2023, 19, 1615–1619. doi:10.3762/bjoc.19.118 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 23, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alkaloids azabicycles Heck reaction iron complex tropone Full Research Paper Source Type: research

Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect
In this study, three new sulfur-containing spiroketals – breynin J (1), epibreynin J (2), and probreynogenin (3) – along with four known compounds – probreynin I (4), phyllaemblic acid (5), breynin B (6), and epibreynin B (7) – were isolated from the roots of Breynia disticha. The structures of compounds 1–7 were elucidated by extensive 1D and 2D NMR spectroscopic analyses, including 1D total correlation spectroscopy (TOCSY), HSQC, HMBC, double quantum-filtered (DQF)-COSY, heteronuclear two-bond correlation (H2BC), and HSQC-TOCSY experiments, as well as high-resolution electrospray ionization ...
Source: Beilstein Journal of Organic Chemistry - October 19, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: anti-inflammatory Breynia disticha RAW 264.7 cells sesquiterpenoids sulfur-containing compounds Full Research Paper Source Type: research

Radical chemistry in polymer science: an overview and recent advances
Abstract Radical chemistry is one of the most important methods used in modern polymer science and industry. Over the past century, new knowledge on radical chemistry has both promoted and been generated from the emergence of polymer synthesis and modification techniques. In this review, we discuss radical chemistry in polymer science from four interconnected aspects. We begin with radical polymerization, the most employed technique for industrial production of polymeric materials, and other polymer synthesis involving a radical process. Post-polymerization modification, including polymer crosslinking and polymer surface m...
Source: Beilstein Journal of Organic Chemistry - October 18, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: crosslinking polymer surface modification post-polymerization modification radical chemistry radical polymerization Review Source Type: research

C – H bond functionalization: recent discoveries and future directions
Beilstein J. Org. Chem. 2023, 19, 1568–1569. doi:10.3762/bjoc.19.114 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 17, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: C – H bond functionalization Editorial Source Type: research

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration
Abstract Cyclodextrins (CDs) are known for their ability to extract lipid components from synthetic and biological membranes and therefore to induce an increase of membrane permeability. However, the effect of cholesterol (CHOL) content in the membrane on the CD permeabilizing effect was not considered yet. Given that an increase in CHOL content reduces the membrane permeability, the aim of this work was to reveal how CHOL would modulate the CDs effect on the membrane. Hence, liposomes made of dipalmitoyl phosphatidylcholine (DPPC) and various CHOL contents (DPPC/CHOL 100:10, 100:25, 100:50, and 100:100) encapsulating the ...
Source: Beilstein Journal of Organic Chemistry - October 17, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cholesterol cyclodextrins liposome membrane permeability Full Research Paper Source Type: research

Lewis acid-promoted direct synthesis of isoxazole derivatives
Abstract Isoxazole derivatives were synthesized via a one-pot method utilizing 2-methylquinoline derivatives as template substrates, sodium nitrite as a nitrogen-oxygen source, and solely using aluminum trichloride as the additive. This approach circumvents the need for costly or highly toxic transition metals and presents a novel pathway for the synthesis of isoxazole derivatives. Beilstein J. Org. Chem. 2023, 19, 1562–1567. doi:10.3762/bjoc.19.113 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 16, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aluminum trichloride Lewis acid isoxazole derivatives sodium nitrite transition metals Full Research Paper Source Type: research

Secondary metabolites of Diaporthe cameroonensis, isolated from the Cameroonian medicinal plant Trema guineensis
Abstract From a fresh root of Trema guineensis (Ulmaceae), endophytic fungi were isolated, among which a taxon belonging to the new species Diaporthe cameroonensis. This strain was fermented in shake flask batch cultures and the broth was extracted with ethyl acetate. From the crude extract, a hemiketal polyketide 1, and an acetylated alternariol 2 were isolated, along with fifteen known secondary metabolites. Their structures were established by extensive NMR spectroscopy and mass spectrometry analyses, as well as by comparison with literature data of their analogs. Beilstein J. Org. Chem. 2023, 19, 1555–1561. ...
Source: Beilstein Journal of Organic Chemistry - October 13, 2023 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alternariol Diaporthe endophytic fungi hemiketal polyketide Full Research Paper Source Type: research