Biobased carbon dots as photoreductants – an investigation by using triarylsulfonium salts

• Valentina Benazzi,
• Arianna Bini,
• Ilaria Bertuol,
• Mariangela Novello,
• Federica Baldi,
• Matteo Hoch,
• Alvise Perosa and
• Stefano Protti

Beilstein J. Org. Chem. 2025, 21, 1024–1030, doi:10.3762/bjoc.21.84

• approach, CDs arise from the decomposition of large carbogenic structures (including graphite, graphite sheets and carbon nanotubes), whereas in the bottom-up approach such materials are obtained by carbonization of small organic molecules and biowastes (carbohydrates, polymers, bioorganic compounds

• voltammetry of triarylsulfonium salts and NMR spectra. Funding Fondazione Cariplo (Photo and Mechano-Chemistry for the Upgrading of Agro- and Sea-food Waste to advanced polymers and nanocarbon materials, CUBWAM, project 2021–0751).

On the photoluminescence in triarylmethyl-centered mono-, di-, and multiradicals

• Daniel Straub,
• Markus Gross,
• Mona E. Arnold,
• Julia Zolg and
• Alexander J. C. Kuehne

Beilstein J. Org. Chem. 2025, 21, 964–998, doi:10.3762/bjoc.21.80

Acyclic cucurbit[n]uril bearing alkyl sulfate ionic groups

• Christian Akakpo,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 717–726, doi:10.3762/bjoc.21.55

• and water [1][2][3][4]. Building on this fundamental knowledge, supramolecular chemists created a variety of functional systems including supramolecular polymers, sensing ensembles, molecular machines, supramolecular separation phases, and drug delivery systems [5][6][7][8][9]. A primary subfield of

Beyond symmetric self-assembly and effective molarity: unlocking functional enzyme mimics with robust organic cages

• Keith G. Andrews

Beilstein J. Org. Chem. 2025, 21, 421–443, doi:10.3762/bjoc.21.30

• imprinted polymers (MIPs) [60] has been discussed elsewhere and will not be covered. Perspective Cavity catalysis: current state of the art Functionalized macrocycles Since Cramer’s work with cyclodextrins [61][62][63], there has been significant interest in using macrocyclic confinement to modulate

The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• participating group. Irrespective of the mechanism, it has been used to prepare pure (1,3)-β-glucan polymers. Chloroacetyl and orthogonal protecting groups: There are other ester-type groups that establish neighbouring group participation when placed in the C-2 position of glycosyl donors, yet differentiate

Oxidation of [3]naphthylenes to cations and dications converts local paratropicity into global diatropicity

• Abel Cárdenas,
• Zexin Jin,
• Yong Ni,
• Jishan Wu,
• Yan Xia,
• Francisco Javier Ramírez and
• Juan Casado

Beilstein J. Org. Chem. 2025, 21, 277–285, doi:10.3762/bjoc.21.20

• shift (NICS) calculations and anisotropy of the current induced density (ACID) plots, as they evidenced the presence of a perimetral diatropic global ring current upon oxidation. Keywords: ACID; aromaticity; force constants; NICS; spectroscopy; Introduction Since the discovery of conjugated polymers

• systems in which charge defects are responsible for conductivity in their corresponding conducting polymers. Acenes are the archetypal structure of small polycyclic aromatic hydrocarbons with a π-electron structure expanded over a sequence of linearly fused benzenes [4]. Whereas acenes, up to substituted

Heteroannulations of cyanoacetamide-based MCR scaffolds utilizing formamide

• Marios Zingiridis,
• Danae Papachristodoulou,
• Despoina Menegaki,
• Konstantinos G. Froudas and
• Constantinos G. Neochoritis

Beilstein J. Org. Chem. 2025, 21, 217–225, doi:10.3762/bjoc.21.13

• be established as a C1 feedstock. [25]. Its high polarity and dielectric constant (it is miscible with water) [26], with the ability to solubilize a wide range of reagents, from salts to polymers, proteins and saccharides, renders formamide an excellent C1 building block [25][27]. Thus, our target

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

• Seungmin Lee,
• Minsuk Kim,
• Hyewon Han and
• Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

• leads to the formation of the N-acyl amidine product 10. 1.4 N-Arylation of dioxazolones Amides bearing N-substituents are key structural motifs in a wide range of polymers [82], natural products [83], and pharmaceuticals [84][85]. Conventional synthetic routes for N-arylamides typically involve the

Hydrogen-bonded macrocycle-mediated dimerization for orthogonal supramolecular polymerization

• Wentao Yu,
• Zhiyao Yang,
• Chengkan Yu,
• Xiaowei Li and
• Lihua Yuan

Beilstein J. Org. Chem. 2025, 21, 179–188, doi:10.3762/bjoc.21.10

• Wentao Yu Zhiyao Yang Chengkan Yu Xiaowei Li Lihua Yuan College of Chemistry, Sichuan University, Chengdu 610064, China 10.3762/bjoc.21.10 Abstract Orthogonal self-assembly represents a useful methodology to construct supramolecular polymers with AA- and AB-type monomers, as commonly used for

• covalently linked polymers. So far, the design of such monomers has relied heavily on three-dimensional macrocycles, and the use of two-dimensional shape-persistent macrocycles for this purpose remains rather rare. Here, we demonstrate a dimerization motif based on a hydrogen-bonded macrocycle that can be

• effectively applied to form orthogonal supramolecular polymers. The macrocycle-mediated connectivity was confirmed by single-crystal X-ray diffraction, which revealed a unique 2:2 binding motif between host and guest, bridged by two cationic pyridinium end groups through π-stacking interactions and other

Hot shape transformation: the role of PSar dehydration in stomatocyte morphogenesis

• Remi Peters,
• Levy A. Charleston,
• Karinan van Eck,
• Teun van Berlo and
• Daniela A. Wilson

Beilstein J. Org. Chem. 2025, 21, 47–54, doi:10.3762/bjoc.21.5

• ) in biomedical applications, boasting advantages in biocompatibility and degradability. While the self-assembly behavior of block copolymers containing polysarcosine-containing polymers has been reported, their potential for shape transformation remains largely untapped, limiting their versatility

• broadening their potential applications in drug delivery and nanotechnology. Our findings shed light on the unique capabilities of polysarcosine-based polymers, paving the way for further exploration and harnessing of their distinctive properties in biomedical research. Keywords: biodegradable; poly(benzyl

• of the non-degradable PEG segment is still ongoing as PEG is regarded as the benchmark for hydrophilic polymers used in drug delivery [7]. The non-biodegradability of PEG under most conditions, coupled with recently discovered immunogenic responses to it, has led to increasing concerns [8][9]. This

Emerging trends in the optimization of organic synthesis through high-throughput tools and machine learning

• Pablo Quijano Velasco,
• Kedar Hippalgaonkar and
• Balamurugan Ramalingam

Beilstein J. Org. Chem. 2025, 21, 10–38, doi:10.3762/bjoc.21.3

• this robotic system promises remarkable applications in materials, polymers, and chemical synthesis. Most automated synthesis platforms are based on expensive scientific equipment, have a large equipment footprint, and need extensive reconfiguration to adapt to new synthetic protocols. To address this

Efficient synthesis of fluorinated triphenylenes with enhanced arene–perfluoroarene interactions in columnar mesophases

• Yang Chen,
• Jiao He,
• Hang Lin,
• Hai-Feng Wang,
• Ping Hu,
• Bi-Qin Wang,
• Ke-Qing Zhao and
• Bertrand Donnio

Beilstein J. Org. Chem. 2024, 20, 3263–3273, doi:10.3762/bjoc.20.270

• reaction. This “palladium-free” reaction between 2Li-BPn and C6F5–C6F5 possesses several advantages: easily available starting chemicals, low cost, efficient, and versatile, displaying the potential to synthesize more complicated fluoroarene molecules and polymers. These fluorine-containing triphenylenes

Cyclodextrin-based rotaxanes for polymer materials: challenge on simultaneous realization of inexpensive production and defined structures

• Yosuke Akae

Beilstein J. Org. Chem. 2024, 20, 3026–3049, doi:10.3762/bjoc.20.252

• -0083 Tokyo, Japan 10.3762/bjoc.20.252 Abstract Owing to their dynamic natures, rotaxane-based polymers are attractive motifs for developing stimuli-responsive materials. However, the accurate control of the rotaxane structure, which can be achieved via multistep synthesis, is key to utilizing the

• material. Concurrently, implementing a scale-up synthesis procedure to exploit the application potential of rotaxane-based polymers induces structural ambiguities, thereby presenting a significant trade-off between realizing inexpensive production and defined structures. To overcome this rotaxane-synthesis

• challenge, cyclodextrin (CD) can be employed as a promising alternative owing to its low production cost. Thus, this study presents an overview of the precise synthesis of CD-based rotaxane and its application to polymers to simultaneously ensure inexpensive production and realize defined structures

Advances in radical peroxidation with hydroperoxides

• Oleg V. Bityukov,
• Pavel Yu. Serdyuchenko,
• Andrey S. Kirillov,
• Gennady I. Nikishin,
• Vera A. Vil’ and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2024, 20, 2959–3006, doi:10.3762/bjoc.20.249

• range of polymers [1]. They are also applied as curing, hardening and crosslinking agents [2]. Global demand for organic peroxides is expected to increase as the use of engineered plastics increases and production capacity is expanded. In addition, the need for polymers is expected to increase due to

gem-Difluorovinyl and trifluorovinyl Michael acceptors in the synthesis of α,β-unsaturated fluorinated and nonfluorinated amides

• Monika Bilska-Markowska,
• Marcin Kaźmierczak,
• Wojciech Jankowski and
• Marcin Hoffmann

Beilstein J. Org. Chem. 2024, 20, 2946–2953, doi:10.3762/bjoc.20.247

• using organolithium reagents (Scheme 1), revealing new avenues in fluorinated unsaturated amide synthesis, which are present in numerous natural products, pharmaceuticals, and polymers [34][35][36][37][38]. The obtained α,β-unsaturated amides may represent promising structural motifs for further

N-Glycosides of indigo, indirubin, and isoindigo: blue, red, and yellow sugars and their cancerostatic activity

• Peter Langer

Beilstein J. Org. Chem. 2024, 20, 2840–2869, doi:10.3762/bjoc.20.240

• ][9][10]. In this context, the best CDK2 inhibitory activities were observed for indirubin-derived oximes [11]. Yellow colored isoindigo received a lot of attention as constituent of polymers applied as semi-conducting materials, organic light emitting materials (OLED), and for related applications

Anion-dependent ion-pairing assemblies of triazatriangulenium cation that interferes with stacking structures

• Yohei Haketa,
• Takuma Matsuda and
• Hiromitsu Maeda

Beilstein J. Org. Chem. 2024, 20, 2567–2576, doi:10.3762/bjoc.20.215

• . Moreover, the N-aryl-substituted TATA+ cations have been used as the building units of porous organic polymers for capturing CO2 [27]. Cations with characteristic electron-deficient planar triangular geometries were used as scaffolds for various supramolecular cage structures [28][29]. Although

HFIP as a versatile solvent in resorcin[n]arene synthesis

• Hormoz Khosravi,
• Valeria Stevens and
• Raúl Hernández Sánchez

Beilstein J. Org. Chem. 2024, 20, 2469–2475, doi:10.3762/bjoc.20.211

• , e.g., polymers and capsules [80]. In that regard, 2,6-dihydroxybenzoic acid is known to also yield inseparable mixtures [9][81]. However, a couple of reports describe successful syntheses with reaction yields ≈40% using 2,6-dihydroxybenzoic acid and formaldehyde under basic conditions [38]. Recently

Cell-free protein synthesis with technical additives – expanding the parameter space of in vitro gene expression

• Tabea Bartsch,
• Stephan Lütz and
• Katrin Rosenthal

Beilstein J. Org. Chem. 2024, 20, 2242–2253, doi:10.3762/bjoc.20.192

• osmolarity using ten different technical additives including organic solvents, polymers, and salts. It is shown that the synthesis of two model proteins, namely superfolder GFP (sfGFP) and the enzyme truncated human cyclic GMP-AMP synthase fused to sfGFP (thscGAS-sfGFP), is very robust against most of the

• alcohols, polyols, polyions or polymers, has a positive effect on protein stability and the soluble fraction expressed with CFPS [17]. The variable composition of CFPS systems with a high number of ingredients and possible reaction conditions [13] thus opens a large parameter space. In addition, non

• some of the gaps in the consideration of the general physical properties and potential effects on the performance of Escherichia coli-based CFPS. We use technical additives, such as water-soluble macromolecular polymers and salts, which are commonly used as deep eutectic solvents (DES) and extend the

Metal-free double azide addition to strained alkynes of an octadehydrodibenzo[12]annulene derivative with electron-withdrawing substituents

• Naoki Takeda,
• Shuichi Akasaka,
• Susumu Kawauchi and
• Tsuyoshi Michinobu

Beilstein J. Org. Chem. 2024, 20, 2234–2241, doi:10.3762/bjoc.20.191

• introduced into octadehydrodibenzo[12]annulene. In this report, the synthesis of new octadehydrodibenzo[12]annulene derivatives, regioselective double addition of organic azides, and an application to crosslinking polymers are described. Keywords: annulene; click chemistry; polymerization; strain-promoted

• ], and crosslinked polymers [14][15][16][17]. Since crosslinking polymers requires high reaction efficiency under mild conditions, developing such reactions is crucial. We previously reported the regioselective double azide addition to octadehydrodibenzo[12]annulene with hexyloxy substituents (DBA-OHex

• the strain-promoted double azide addition feature, DBA 5 was evaluated as a crosslinker for azidated polymers. After 5 (5 mol %) was added to a partially azidated poly(vinyl chloride) (PVC-N3) (x = 0.11, n = 1000) in THF, the solvent was gradually evaporated on a Teflon boat. The resulting self

O,S,Se-containing Biginelli products based on cyclic β-ketosulfone and their postfunctionalization

• Kateryna V. Dil and
• Vitalii A. Palchykov

Beilstein J. Org. Chem. 2024, 20, 2143–2151, doi:10.3762/bjoc.20.184

• organic and medicinal chemists. DHPMs are found in a variety of marine-sourced alkaloids, which are essential for creating biologically active natural products [10]. Some of the DHPM derivatives are also known as functional polymers, adhesives, and fabric dyes [8][12]. In recent decades, the scope of the

Factors influencing the performance of organocatalysts immobilised on solid supports: A review

• Zsuzsanna Fehér,
• Dóra Richter,
• Gyula Dargó and
• József Kupai

Beilstein J. Org. Chem. 2024, 20, 2129–2142, doi:10.3762/bjoc.20.183

• ]. The role of the polymers as supports for catalysts is not merely passive. These supports significantly influence the reaction environment and catalytic efficiency [42]. Attachment methods, spacer lengths, and polymer nature profoundly impact the catalyst's performance and recyclability. Various

• immobilization strategies, including covalent bonding and encapsulation, cater to different polymer types. Soluble polymers enhance diffusion, while insoluble ones ensure stability and high loading capacities [42]. Silica is also widely applied due to its ease of functionalisation and thermal stability [43]. The

• modifications play a more important role. MOFs are a type of porous crystalline polymers where organic ligands are coordinated to metal clusters [80][81][82][83][84][85][86][87][88][89][90]. The framework can be post-synthetically modified by functional organic sites, often specifically chiral functionalities

Computational toolbox for the analysis of protein–glycan interactions

• Ferran Nieto-Fabregat,
• Maria Pia Lenza,
• Angela Marseglia,
• Cristina Di Carluccio,
• Antonio Molinaro,
• Alba Silipo and
• Roberta Marchetti

Beilstein J. Org. Chem. 2024, 20, 2084–2107, doi:10.3762/bjoc.20.180

• python framework that allows users to prepare carbohydrate structures for atomistic simulations of complex glycoproteins, glycolipids and carbohydrate polymers in the GROMACS force field format (see below). Polysaccharides can be prepared by using the prepreader.py tool, glycoproteins and glycolipids by

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

• Ignaz Betcke,
• Alissa C. Götzinger,
• Maryna M. Kornet and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

• consecutive three-component approach in a polymer analogous fashion with diynes 105, terephthaloyl chloride (106), and hydrazines to synthesize high molecular weight pyrazole-based polymers 107 (Scheme 38) [132]. The materials 107 fluoresce in THF solutions, form thin films, and possess high thermal stability

The Groebke–Blackburn–Bienaymé reaction in its maturity: innovation and improvements since its 21st birthday (2019–2023)

• Cristina Martini,
• Muhammad Idham Darussalam Mardjan and
• Andrea Basso

Beilstein J. Org. Chem. 2024, 20, 1839–1879, doi:10.3762/bjoc.20.162

• GBB products were introduced to the subsequent reactions in the same pot without isolating them from the reaction mixture. In the one-pot multicomponent reaction, three substrates with di- or tri-functional groups were engaged in the GBB reaction to produce the heterocyclic polymers. Panda and

• (41–67%). Multicomponent polymerizations are simple and efficient methods to construct a library of polymers with great structural complexity and diversity, including fused-heterocyclic polymers[64]. Tang et al. [65] reported the transition-metal-free multicomponent polymerization of dialdehydes 96a–c

• and diisocyanides 97a,b in the presence of 2-aminopyridine (1, Scheme 30). The polymerization was carried out under mild conditions (in ethanol as the solvent and p-TsOH as the catalyst) and delivered six polymers featured with high yields (up to 98%), molecular weight (up to 41,700 g/mol), atom