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

• . Overall, this review presents a first detailed account of the electron transport properties of Qx derivatives in recent times, offering valuable insights into their potential as promising ETMs. Review Quinoxalines as polymer acceptors The development of efficient and high-performing polymer materials

• based on Qxs is of significant interest in the field of organic electronics. A compelling indication of this potential is the remarkable achievements made by a relatively simple polymer, poly[(thiophene)-alt-(6,7-difluoro-2-(2-hexyldecyloxy)quinoxaline)] (PTQ10). PTQ10 has demonstrated impressive power

• conversion efficiencies (PCEs) of over 12% in polymer solar cells (PCS) when paired with the IDT acceptor [15], over 16% with the Y6 acceptor [16][17] and a champion PCE of 21.2% in perovskite solar cells [18]. This outstanding performance is attributed to the versatile and tunable nature of the Qx moiety

Benzoimidazolium-derived dimeric and hydride n-dopants for organic electron-transport materials: impact of substitution on structures, electrochemistry, and reactivity

• Swagat K. Mohapatra,
• Khaled Al Kurdi,
• Samik Jhulki,
• Georgii Bogdanov,
• John Bacsa,
• Maxwell Conte,
• Tatiana V. Timofeeva,
• Seth R. Marder and
• Stephen Barlow

Beilstein J. Org. Chem. 2023, 19, 1651–1663, doi:10.3762/bjoc.19.121

• ]. V derivatives have also been obtained as pyrolysis products of a variety of Y = aryl 1H derivatives [33], while Vb has also been found to be both a solution decomposition product of 1bH [27][34] and a beneficial additive for a 1bH-doped polymer [27], and has been crystallographically characterized

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• . Osuka and co-workers provided novel insight into the meso-appended crown ether porphyrins, namely, chromophore-incorporated and polymer-based systems capable of acting as multitopic receptors for transition, alkali, and alkali-earth metal cations, which were proved as optical sensing agents among other

Radical chemistry in polymer science: an overview and recent advances

• Zixiao Wang,
• Feichen Cui,
• Yang Sui and
• Jiajun Yan

Beilstein J. Org. Chem. 2023, 19, 1580–1603, doi:10.3762/bjoc.19.116

• Zixiao Wang Feichen Cui Yang Sui Jiajun Yan School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Rd., Shanghai, 201210, China 10.3762/bjoc.19.116 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 modification, is the key process that introduces functionality and practicality to polymeric

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

Visible-light-induced nickel-catalyzed α-hydroxytrifluoroethylation of alkyl carboxylic acids: Access to trifluoromethyl alkyl acyloins

• Feng Chen,
• Xiu-Hua Xu,
• Zeng-Hao Chen,
• Yue Chen and
• Feng-Ling Qing

Beilstein J. Org. Chem. 2023, 19, 1372–1378, doi:10.3762/bjoc.19.98

• Feng Chen Xiu-Hua Xu Zeng-Hao Chen Yue Chen Feng-Ling Qing Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China Shandong Dongyue Polymer Material Co., Ltd

Organic thermally activated delayed fluorescence material with strained benzoguanidine donor

• Alexander C. Brannan,
• Elvie F. P. Beaumont,
• Nguyen Le Phuoc,
• George F. S. Whitehead,
• Mikko Linnolahti and
• Alexander S. Romanov

Beilstein J. Org. Chem. 2023, 19, 1289–1298, doi:10.3762/bjoc.19.95

• Information File 1). The photoluminescence (PL) characteristics of 4BGIPN have been studied in methylcyclohexane solution (MCH, concentration 3.2 × 10−5 M) and Zeonex polymer films (0.1% concentration by weight) at 298 K and 77 K, which is shown in Figure 5 with data collected in Table 3. Compound 4BGIPN

• providing ZEONEX® 480 Cyclo Olefin Polymer (COP) used in our studies. We are grateful to Dr. Louise Natrajan at the University of Manchester for providing access to FLS-1000 fluorometer. Funding This work was supported by the Royal Society and the Academy of Finland. A.S.R. acknowledges support from the

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• 2020, Pedrosa and co-workers devised a chiral heterogenous thiourea catalyst that was applied in an enantioefficient aza-Friedel–Crafts process. A series of heterogenous catalysts were prepared by condensation between alkaloids and polystyrene-derived isothiocyanates. These polymer-supported materials

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• . This methodology has been applied to diverse areas of chemistry, including natural product synthesis [45][46], medicinal chemistry [47][48], polymer chemistry [49][50] and porphyrin chemistry [51][52][53]. In recent years, green chemistry has become a widely used method for organic synthesis in order

• a mechanism for this protocol as shown in Scheme 38b. Conclusion The synthesis of pyrrole derivatives has piqued the interest of many synthetic researchers as they offer promising applications in pharmaceutical, polymer, and natural product chemistry. The introduction of a pyrrole moiety into a

• pharmaceutically active molecules, polymer synthesis, total synthesis of natural products, porphyrin functionalization, and the synthesis of various pyrrole-containing heterocyclic molecules. We believe that this review will be useful and will encourage researchers to apply the modified Clauson–Kaas reaction to

Cyclodextrins as building blocks for new materials

• Miriana Kfoury and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2023, 19, 889–891, doi:10.3762/bjoc.19.66

• biocompatible. Thus, these supra-architectures have a multitude of uses in food, biomedicine, regenerative medicine, cosmetics, molecular electronics, polymer chemistry, gold recovery, gas absorption, depollution, biochemical material sciences, nanotechnology, self-healing materials, 3D printing, and so on [19

Light-responsive rotaxane-based materials: inducing motion in the solid state

• Adrian Saura-Sanmartin

Beilstein J. Org. Chem. 2023, 19, 873–880, doi:10.3762/bjoc.19.64

• ) Chemical structure of polyrotaxane 2; and (b) cartoon representation of the light-triggered degradation of rotaxane polymer 2 [52]. The key colour of the cartoon representation is analogous to that of the chemical structures. a) Chemical structures of rotaxanes (E)-3 and (Z)-3; b) stick representation of

pH-Responsive fluorescent supramolecular nanoparticles based on tetraphenylethylene-labelled chitosan and a six-fold carboxylated tribenzotriquinacene

• Nan Yang,
• Yi-Yan Zhu,
• Wei-Xiu Lin,
• Yi-Long Lu and
• Wen-Rong Xu

Beilstein J. Org. Chem. 2023, 19, 635–645, doi:10.3762/bjoc.19.45

• labelling of hydrophobic TPE fluorogens, reducing the affinity of the CS chains to the aqueous medium and resulting in the entanglement or wrapping of the TPE fluorogens by polymer chains. As a result, the RIR process was enhanced, greatly increasing the fluorescence. In addition, the fluorescence intensity

• improved water solubility of the supra-amphiphile due to the highly water-soluble behavior of TBTQ-C6 under alkaline conditions in its carboxyl anion form. As a result, the polymer chains were extended, releasing the entanglement and wrapping of the TPE fluorogens, thereby reducing the emission of the

• successfully designed and synthesized different degrees of TPE-labelled CS polymer compounds that exhibit the AIE fluorescence effect and we constructed pH-responsive fluorescent supramolecular spherical nanoparticles based on CS-TPE alone and the host–guest TBTQ-C6/CS-TPE supra-amphiphile. The critical

Discrimination of β-cyclodextrin/hazelnut (Corylus avellana L.) oil/flavonoid glycoside and flavonolignan ternary complexes by Fourier-transform infrared spectroscopy coupled with principal component analysis

• Nicoleta G. Hădărugă,
• Gabriela Popescu,
• Dina Gligor (Pane),
• Cristina L. Mitroi,
• Sorin M. Stanciu and
• Daniel Ioan Hădărugă

Beilstein J. Org. Chem. 2023, 19, 380–398, doi:10.3762/bjoc.19.30

• cannabinus L.) seed oil or “Persian lilac” (Melia azedarach L.) seed oil. The oils were complexed by spray drying using β-CD/gum arabic/sodium caseinate or a β-CD polymer, respectively [22][23]. However, there are less studies on the CD encapsulation of non-volatile vegetable oils in comparison with

• biologically active molecules on CD-coated polymers used in chromatography [62]. PCA was used for the evaluation of the similarity/dissimilarity of some pesticides, especially fungicides and herbicides, using the effect of a water-soluble β-CD polymer on the apparent pesticide’s lipophilicity [63]. Also

CuAAC-inspired synthesis of 1,2,3-triazole-bridged porphyrin conjugates: an overview

• Dileep Kumar Singh

Beilstein J. Org. Chem. 2023, 19, 349–379, doi:10.3762/bjoc.19.29

• hydrophilic triazole-linked porphyrin-polymer conjugates (PPCs) (Scheme 28). The PPCs 137 and 139 were prepared by the reaction between tetraazido-Zn-porphyrin 135 or diazido-Zn-porphyrin 138 with polymers 136 bearing various hydrophilic and hydrophobic substituents using CuSO4∙4H2O and ascorbic acids under

• -bridged porphyrin-β-CD conjugate 126. Synthesis of meso-triazole-bridged porphyrin star trimer 129. Synthesis of 1,2,3-triazole-linked porphyrin-β-CD conjugates 131a,b. Synthesis of tritriazole-bridged porphyrin-lantern-DNA sequence 134. Synthesis of meso-triazole-linked porphyrin-polymer conjugates 137

Investigation of cationic ring-opening polymerization of 2-oxazolines in the “green” solvent dihydrolevoglucosenone

• Solomiia Borova and
• Robert Luxenhofer

Beilstein J. Org. Chem. 2023, 19, 217–230, doi:10.3762/bjoc.19.21

• Solomiia Borova Robert Luxenhofer Functional Polymer Materials, Chair for Advanced Materials Synthesis, Institute for Functional Materials and Biofabrication, Department of Chemistry and Pharmacy, Julius-Maximilans-University of Würzburg, Röntgenring 11, 97070 Würzburg, Germany Soft Matter

• reasons [1]. Halogenated solvents such as chlorobenzene or dichloromethane are widely used in polymer production, but their toxicity and high energy consumption for synthesis make them unwanted for widespread commercial use. Many other dipolar solvents such as dimethyl sulfoxide (DMSO), N,N

• biomedical applications, in particular as an alternative to the hydrophilic poly(ethylene glycol) (PEG), which is the polymer of choice for many biomedical applications due to its high solubility, low cytotoxicity and biocompatibility [3][4][5][6][7][8][9]. However, an ongoing discussion about pre-existing

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

• through either (i) the cationic nature of the CD such as poly-β-CD-C6 or (ii) coating of non-ionic 6-O-capro-β-CD with the cationic polymer chitosan (CS). Uncoated 6-O-capro-β-CD negatively charged NPs were used as control formulation. Results and Discussion Fabrication and in vitro characterization of

• the relaxation of the polymer chain begins and accelerates the release in SIF. When a further evaluation was made for the CS-(6-O-capro-β-CD), which showed a high correlation between the two models, the diffusional exponent values of the Korsmeyer–Peppas and Peppas–Sahlin models were calculated as

• 1.039 and 0.450, respectively. Similarly, the n value of Korsmeyer–Peppas above 0.85 indicates that the release mechanism is realized by super case II [44]. This value was interpreted as indicative of the release seen with the erosion of the nanoparticle material and the initiation of polymer relaxation

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

• Naoya Oku,
• Saki Hayashi,
• Yuji Yamaguchi,
• Hiroyuki Takenaka and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2023, 19, 133–138, doi:10.3762/bjoc.19.13

• , antifoamers, preservatives, antistatic agents, polymer lubricants, and mold-releasing agents for the production of foods, cosmetics, ointments, paints, and plastics [33]. Compound 1 exhibited antibacterial activity, evaluated by a microculture method, with MIC 50 μg/mL against B. subtilis ATCC6633 and 100 μg

• ) to see the separation of activity at the top two and slow-eluting fractions. The top fraction was purified by repeated HPLC first on an ODS column (Cosmosil AR-II 1 × 25 cm) and second on a styrene-divinylbenzene polymer column (Hamilton PRP-1 1 × 25 cm) both eluted with MeCN/50 mM NaClO4 75:25 to

Inline purification in continuous flow synthesis – opportunities and challenges

• Jorge García-Lacuna and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 1720–1740, doi:10.3762/bjoc.18.182

• chromatography system which utilizes multiple columns in parallel with a series of valves to stagger the injection of crude material to each of the column lines. The columns are filled with a diethylaminopropyl-functionalized polymer, followed by an UV–vis detector to identify and separate the different peaks

• heterogeneous fashion. This oftentimes leads to improved green credentials, safety, and sometimes efficiency, especially when it is applied to the downstream process. Commercially available resins, activated charcoal, polymer-supported species that trap spent reagents or side-products as well as related

Molecular and macromolecular electrochemistry: synthesis, mechanism, and redox properties

• Shinsuke Inagi and
• Mahito Atobe

Beilstein J. Org. Chem. 2022, 18, 1505–1506, doi:10.3762/bjoc.18.158

• , polymer electrolyte membrane electrolysis technology, and new methods coupled with photoredox catalysts or transition metal catalysis, resulting in remarkable progress in organic electrosynthetic processes. Theoretical calculations have also led to a better understanding of the electron transfer behavior

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

• how available Cu-based electrosynthetic reactions can be used to calibrate electrochemical signals on a polymer-coated electrode array and delineate the factors to be considered when choosing a polymer surface for such a study. Keywords: calibration of binding curves; electrochemical signaling

• development of polymer-coated arrays that capitalize on the versatility of diblock copolymers as surface coatings (Figure 2) [17][18][19]. In the polymer, one of the blocks is used to place attachment sites for molecules above the electrodes (the arylbromide or arylborate block in the polymer shown), and the

• other block is used to provide a site for cross-linking the polymer in order to render the surface more stable once it is coated onto an array (the cinnamate block is used to make a polymer network through photochemical cross-linking). The use of the borate ester surface provides a tunable surface that

1,4,6,10-Tetraazaadamantanes (TAADs) with N-amino groups: synthesis and formation of boron chelates and host–guest complexes

• Artem N. Semakin,
• Ivan S. Golovanov,
• Yulia V. Nelyubina and
• Alexey Yu. Sukhorukov

Beilstein J. Org. Chem. 2022, 18, 1424–1434, doi:10.3762/bjoc.18.148

• dynamic covalent libraries [25]. TAAD can be covalently bound to a polymer matrix through the nucleophilic nitrogen N(1) that was used to prepare scavengers of boronic acids [25]. Also, TAAD was demonstrated to serve as a scorpionate-type ligand for manganese and iron leading to complexes with the metal

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups

• Neda Rafieiolhosseini,
• Matthias Killa,
• Thorben Neumann,
• Niklas Tötsch,
• Jean-Noël Grad,
• Alexander Höing,
• Thies Dirksmeyer,
• Jochen Niemeyer,
• Christian Ottmann,
• Shirley K. Knauer,
• Michael Giese,
• Jens Voskuhl and
• Daniel Hoffmann

Beilstein J. Org. Chem. 2022, 18, 1322–1331, doi:10.3762/bjoc.18.137

• electrostatic potential grid into energy grids suitable for the Hamiltonian, chemically relevant polymer fragments were used as molecular probes in Epitopsy [26]. Epitopsy is a tool designed to calculate the electrostatic energy of a protein–ligand system from the protein potential grid and ligand charge

• in the context of polymer studies [33][34][35]. Our model is a chain of five beads, GCP-Lys-AIE-Lys-GCP, with each pair of neighbors in the chain connected by a harmonic spring potential (Figure 1b). Given the symmetry of 1, there are two types of springs, GCP-Lys and Lys-AIE. The spring parameters

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

• Merve Karaman,
• Abhishek Kumar Gupta,
• Subeesh Madayanad Suresh,
• Tomas Matulaitis,
• Lorenzo Mardegan,
• Daniel Tordera,
• Henk J. Bolink,
• Sen Wu,
• Stuart Warriner,
• Ifor D. Samuel and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

• where the emissive layer also contained an inorganic salt and a conducting polymer. Recently, a step-change in device performance were achieved by He et al. who employed a cationic TADF compound that possesses low-lying through-space and through-bond charge transfer excited states [23]. The LEEC showed

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• ; Introduction Polyphosphate (polyP, Figure 1) is a linear polymer of up to thousands of phosphate residues connected by phosphate anhydride bonds. It serves as a phosphate storage molecule and plays a crucial role in biofilm formation and stress responses of cells [1]. So far polyP has been detected in every

Polymer and small molecule mechanochemistry: closer than ever

• José G. Hernández

Beilstein J. Org. Chem. 2022, 18, 1225–1235, doi:10.3762/bjoc.18.128

• (mechanochemistry) can be accomplished through various experimental strategies. Among them, ultrasonication of polymeric matrices and ball milling of reaction partners have become the two leading approaches to carry out polymer and small molecule mechanochemistry, respectively. Often, the methodological differences

• between these practical strategies seem to have created two seemingly distinct lines of thought within the field of mechanochemistry. However, in this Perspective article, the reader will encounter a series of studies in which some aspects believed to be inherently related to either polymer or small

• molecule mechanochemistry sometimes overlap, evidencing the connection between both approaches. Keywords: ball milling; mechanochemistry; mechanophore; polymer; pulsed ultrasonication; Introduction In the past two decades, the growth in popularity of mechanochemistry has been unmistakable. During this