Silica gel with covalently attached bambusuril macrocycle for dicyanoaurate sorption from water

• Michaela Šusterová and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2025, 21, 2604–2611, doi:10.3762/bjoc.21.201

• ]. In the field of anion extraction, there is growing interest in solid-phase substrates functionalized with synthetic macrocyclic receptors. These materials employ a supramolecular approach based on specific host–guest interactions between the immobilized macrocycle and the guest in solution, often

• [10]. Although synthetic anion receptors have attracted increasing attention in the field of supramolecular chemistry, there are still relatively few reports of materials that employ macrocyclic receptors to recognize and selectively bind anionic species specifically in aqueous environments. For

Conformational effects on iodide binding: a comparative study of flexible and rigid carbazole macrocyclic analogs

• Guang-Wei Zhang,
• Yong Zhang,
• Le Shi,
• Chuang Gao,
• Hong-Yu Li and
• Lei Xue

Beilstein J. Org. Chem. 2025, 21, 2369–2375, doi:10.3762/bjoc.21.181

• fluorescence quenching efficiency upon iodide binding compared to the rigid WDG (KPBG/KWDG = 22.78), demonstrating its potential as a highly sensitive optical probe and offering a novel strategy for engineering dynamic supramolecular receptors. Two carbazole-based macrocyclic probes, PBG (flexible benzene ring

• interplay between conformational dynamics and localized structural adaptations governing anion recognition. The findings advance the rational design of tunable, high-affinity anion receptors and deepen the understanding of conformational regulation in supramolecular systems. Keywords: anion recognition

• ; carbazole macrocycles; conformational selection; induced-fit; supramolecular chemistry; Introduction Macrocyclic compounds have garnered significant attention in supramolecular chemistry and anion recognition owing to their tunable cavity geometries and binding capabilities [1][2][3][4][5][6][7][8

Rotaxanes with integrated photoswitches: design principles, functional behavior, and emerging applications

• Jullyane Emi Matsushima,
• Khushbu,
• Zuliah Abdulsalam,
• Udyogi Navodya Kulathilaka Conthagamage and
• Víctor García-López

Beilstein J. Org. Chem. 2025, 21, 2345–2366, doi:10.3762/bjoc.21.179

• three decades, photoswitches have been successfully integrated into a variety of supramolecular architectures, including mechanically interlocked molecules (MIMs) such as rotaxanes, enabling new dynamic functions [6][7]. Rotaxanes are molecules composed of a macrocycle threaded onto a linear axle, with

Insoluble methylene-bridged glycoluril dimers as sequestrants for dyes

• Suvenika Perera,
• Peter Y. Zavalij and
• Lyle Isaacs

Beilstein J. Org. Chem. 2025, 21, 2302–2314, doi:10.3762/bjoc.21.176

• ], and non-conventional adsorbents [14]. Although activated carbon is widely used, its ability to capture polar compounds is limited and the regeneration process is complex and energy-intensive [15]. In work that stimulated supramolecular chemists to enter the game, Dichtel and co-workers demonstrated

Switchable pathways of multicomponent heterocyclizations of 5-amino-1,2,4-triazoles with salicylaldehydes and pyruvic acid

• Yana I. Sakhno,
• Oleksander V. Buravov,
• Kostyantyn Yu. Yurkov,
• Anastasia Yu. Andryushchenko,
• Svitlana V. Shishkina and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2030–2035, doi:10.3762/bjoc.21.158

• materials based on supramolecular systems for biomedical and veterinary applications’ (2023.05/0003).

α-Ketoglutaric acid in Ugi reactions and Ugi/aza-Wittig tandem reactions

• Vladyslav O. Honcharov,
• Yana I. Sakhno,
• Olena H. Shvets,
• Vyacheslav E. Saraev,
• Svitlana V. Shishkina,
• Tetyana V. Shcherbakova and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2025, 21, 2021–2029, doi:10.3762/bjoc.21.157

• materials based on supramolecular systems for biomedical and veterinary applications’ (2023.05/0003).

Systematic pore lipophilization to enhance the efficiency of an amine-based MOF catalyst in the solvent-free Knoevenagel reaction

• Pricilla Matseketsa,
• Margret Kumbirayi Ruwimbo Pagare and
• Tendai Gadzikwa

Beilstein J. Org. Chem. 2025, 21, 1854–1863, doi:10.3762/bjoc.21.144

• efficiency. Keywords: metal-organic frameworks; post-synthesis modification; supramolecular catalysis; Introduction Most enzymatic reactions take place in multifunctional cavities in which multiple amino acid residues work cooperatively to orient and activate reactants [1][2][3]. These residues may also

Photoswitches beyond azobenzene: a beginner’s guide

• Michela Marcon,
• Christoph Haag and
• Burkhard König

Beilstein J. Org. Chem. 2025, 21, 1808–1853, doi:10.3762/bjoc.21.143

• introduction of intramolecular interactions [123]; other solutions are the incorporation in polymers [124] or the confinement in supramolecular cages [125][126]. The thermal stability was found to depend primarily on the nature of the aryl rings: the high aromatic stabilisation energy of phenyl is correlated

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• stimuli have garnered significant interest from researchers and have broad applications in the biomedical field. Aromatic macrocycles, including calixarenes and pillararenes, are considered ideal candidates for the construction of supramolecular drug delivery systems because of their simple synthesis

• , ease of modification, electron-rich and hydrophobic cavities, and highly selective molecular recognition. In recent years, numerous supramolecular drug delivery systems utilizing aromatic macrocycles have been developed. This review article provides an overview of the advancements of controlled drug

• of controlled-release technologies, with the aim of offering a reference for the utilization of aromatic macrocycles in drug-controlled release applications. Keywords: aromatic macrocycle; controlled-release drug delivery systems; stimulus response; supramolecular chemistry; Introduction Drugs are

Unique halogen–π association detected in single crystals of C–N atropisomeric N-(2-halophenyl)quinolin-2-one derivatives and the thione analogue

• Mai Uchibori,
• Nanami Murate,
• Kanako Shima,
• Tatsunori Sakagami,
• Ko Kanehisa,
• Gary James Richards,
• Akiko Hori and
• Osamu Kitagawa

Beilstein J. Org. Chem. 2025, 21, 1748–1756, doi:10.3762/bjoc.21.138

• interaction as an alternative to hydrogen bonding and has been widely used as an important supramolecular tool in broad fields such as materials science, crystal engineering, liquid crystals, synthetic organic chemistry and medicinal chemistry [22][23][24][25][26]. Typically, halogen bonding has been

3,3'-Linked BINOL macrocycles: optimized synthesis of crown ethers featuring one or two BINOL units

• Somayyeh Kheirjou,
• Jan Riebe,
• Maike Thiele,
• Christoph Wölper and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2025, 21, 1719–1729, doi:10.3762/bjoc.21.134

• ). Keywords: BINOL; chirality; crown ethers; macrocycles; supramolecular chemistry; Introduction Crown ethers are at the heart of supramolecular chemistry [1]. Ever since their discovery in 1960, a vast number of different crown ethers has been synthesized and their interactions with guest molecules have

• been studied. The pioneering works in this area by Cram, Lehn and Pedersen marked the beginning of modern supramolecular chemistry and were honoured with the Nobel Prize in Chemistry in 1987 [2][3][4]. Soon, it was realized that chiral crown ethers are highly promising host molecules for

On the aromaticity and photophysics of 1-arylbenzo[a]imidazo[5,1,2-cd]indolizines as bicolor fluorescent molecules for barium tagging in the study of double-beta decay of ¹³⁶Xe

• Eric Iván Velazco-Cabral,
• Fernando Auria-Luna,
• Juan Molina-Canteras,
• Miguel A. Vázquez,
• Iván Rivilla and
• Fernando P. Cossío

Beilstein J. Org. Chem. 2025, 21, 1627–1638, doi:10.3762/bjoc.21.126

• behavior in the emission spectra. Indeed, initial experiments were successful. However, we observed that translation of the behavior of these FBIs from supramolecular chemistry to solid–gas interfaces raises important issues in terms of both discrimination between free and chelated states and photophysical

Advances in nitrogen-containing helicenes: synthesis, chiroptical properties, and optoelectronic applications

• Meng Qiu,
• Jing Du,
• Nai-Te Yao,
• Xin-Yue Wang and
• Han-Yuan Gong

Beilstein J. Org. Chem. 2025, 21, 1422–1453, doi:10.3762/bjoc.21.106

• spectra, underscoring the capability of helicene-based frameworks for anion-responsive chiroptical modulation. These findings highlight how precise structural design and supramolecular engineering can facilitate the development of high-performance, stimuli-responsive chiral luminophores. In 2022, Zhang

Gold extraction at the molecular level using α- and β-cyclodextrins

• Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

• Susana Santos Braga LAQV-REQUIMTE and Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal 10.3762/bjoc.21.89 Abstract Cyclodextrins (CDs) are known for their ability to form supramolecular interactions with a wide range of guest molecules. In this review, focus is given on

• spontaneous complex formation between α-CD and tetrabromoaurate and its current status of use in a few mining sites in the United States. Keywords: bromoaurate; cyanoaurate; cyclodextrin inclusion; self-assembly; supramolecular interactions; Introduction Gold has allured and captivated humankind ever since

• , which still depends solely on the highly pollutant cyanide leaching process. An emerging strategy for gold recovery is through supramolecular chemistry, with studies indicating that macrocycles such as 18-crown-6 [23], cucurbit[6]uril [24], cucurbit[8]uril [25], and cyclodextrins can isolate gold with

Supramolecular assembly of hypervalent iodine macrocycles and alkali metals

• Krishna Pandey,
• Lucas X. Orton,
• Grayson Venus,
• Waseem A. Hussain,
• Toby Woods,
• Lichang Wang and
• Kyle N. Plunkett

Beilstein J. Org. Chem. 2025, 21, 1095–1103, doi:10.3762/bjoc.21.87

• lithium tetrakis(pentafluorophenyl)borate ethyl etherate LiBArF20 and sodium tetrakis[3,5-bis(trifluoromethyl)phenyl]borate NaBArF24. The electron-rich, outwardly projected carbonyl oxygens of the HIM co-crystalize with the cations into bent supramolecular architectures. Both crystal structures show a

• are presented. Keywords: hypervalent iodine; macrocycle; metal coordination; supramolecular; Introduction Supramolecular chemistry is emerging as a pivotal area of research in both medicinal and materials chemistry that opens the avenue for new functionalized materials for their use in medical

• devices or therapeutics [1], drug delivery [2], supramolecular sensing [3], purification [4], and separation [5][6]. The interactions in supramolecular assemblies are driven by well-known hydrogen-bonding, hydrophobic interactions, electrostatic interactions and π–π stacking [7][8]. The supramolecular

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

Dicarboxylate recognition based on ultracycle hosts through cooperative hydrogen bonding and anion–π interactions

• Wen-Hui Mi,
• Teng-Yu Huang,
• Xu-Dong Wang,
• Yu-Fei Ao,
• Qi-Qiang Wang and
• De-Xian Wang

Beilstein J. Org. Chem. 2025, 21, 884–889, doi:10.3762/bjoc.21.72

• Sciences, Beijing 100049, China 10.3762/bjoc.21.72 Abstract The efficient binding of dicarboxylates represents an important yet challenging issue in supramolecular chemistry. In this study, we designed functional ultracycles as hosts to accommodate large organic dicarboxylate anions. These ultracycles

Unraveling cooperative interactions between complexed ions in dual-host strategy for cesium salt separation

• Zhihua Liu,
• Ya-Zhi Chen,
• Ji Wang,
• Qingling Nie,
• Wei Zhao and
• Biao Wu

Beilstein J. Org. Chem. 2025, 21, 845–853, doi:10.3762/bjoc.21.68

• separation [4][5][6][7][8]. Building on the extensive research into anion and cation receptors within the realm of supramolecular chemistry [9][10][11][12], numerous heteroditopic ion-pair receptors have been elaborately developed [13][14][15]. These receptors, consisting of binding sites for both anions and

Carbon-rich materials: from polyaromatic molecules to fullerenes and other carbon allotropes

• Hiroko Yamada and
• Yoko Yamakoshi

Beilstein J. Org. Chem. 2025, 21, 798–799, doi:10.3762/bjoc.21.62

• chemistry, computational chemistry, physics, electrochemistry, polymer chemistry, supramolecular chemistry, and biochemistry. All are working on fascinating topics associated with these exciting molecules. Furthermore, the authors come from all over the world, not only from Switzerland and Japan but also

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

• elements of life processes including self- versus non-self-recognition, biosynthesis, molecular and ion transport, and replication. Beginning with the pioneering works of Pedersen, Lehn, and Cram, supramolecular chemists have studied the fundamental aspects of non-covalent interactions in organic solvents

• 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

• supramolecular chemistry involves the synthesis of macrocyclic hosts and studies of their molecular recognition properties. The most widely studied macrocyclic host systems include those created entirely by covalent bonds (crown ethers, cyclodextrins, calixarenes, cyclophanes, pillararenes, cucurbit[n]urils (CB

Origami with small molecules: exploiting the C–F bond as a conformational tool

• Patrick Ryan,
• Ramsha Iftikhar and
• Luke Hunter

Beilstein J. Org. Chem. 2025, 21, 680–716, doi:10.3762/bjoc.21.54

• ubiquitous molecules in biology. Their functions permeate every aspect of life, including as essential components of oligonucleotide structure; as principal players in metabolism and energy storage; as motifs for the post-translational modification of proteins; and as partners in myriad supramolecular

• ; instead, it is biased towards one particular rotamer due to nO → σ*C1–O5 hyperconjugation. This opportunity for hyperconjugation is lost with the carbasugar glycosides, and hence the anomeric bond in 75 tends to rotate more freely and this can compromise supramolecular binding interactions. However, the

Asymmetric synthesis of β-amino cyanoesters with contiguous tetrasubstituted carbon centers by halogen-bonding catalysis with chiral halonium salt

• Yasushi Yoshida,
• Maho Aono,
• Takashi Mino and
• Masami Sakamoto

Beilstein J. Org. Chem. 2025, 21, 547–555, doi:10.3762/bjoc.21.43

• organic chemistry [2][3][4][5], organocatalysis [6][7], metal catalysis [8][9], biochemistry [10][11], materials science [12][13], and supramolecular chemistry [14][15], although its successful application to asymmetric catalysis has been limited (Figure 1) [16][17][18][19][20]. In 2018, Arai and co

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

• Francesco Mele,
• Ana M. Constantin,
• Andrea Porcheddu,
• Raimondo Maggi,
• Giovanni Maestri,
• Nicola Della Ca’ and
• Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

• surface area exposed to light but also to allow the motions within the crystal. In another instance, MacGillivray and colleagues reported the synthesis of rctt-tetrakis(4-pyridyl)cyclobutane (2.3) via [2 + 2] photodimerization of trans-1,2-bis(4-pyridyl)ethylene (2.1) via supramolecular catalysis by 4,6

• . Mechanochemically triggered pedal-like motion in solid-state [2 + 2] photochemical cycloaddition for the formation of cyclobutanes [62]. Mechanically promoted [2 + 2] photodimerization of trans-1,2-bis(4-pyridyl)ethylene (2.1) via supramolecular catalysis by 4,6-dichlororesorcinol (2.2) in the solid state [64

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

• Keith G. Andrews Department of Chemistry, Durham University, Lower Mount Joy, South Rd, Durham, DH1 3LE, UK 10.3762/bjoc.21.30 Abstract The bespoke environments in enzyme active sites can selectively accelerate chemical reactions by as much as 1019. Macromolecular and supramolecular chemists have

• symmetry to enable promising catalytic modes. Keywords: cavity confinement catalysis; enzyme mimicry; robust organic cages; self-assembly; supramolecular catalysis; Introduction I frequently introduce my research on organic cage enzyme mimics with the following observation. For hundreds of years

• -accelerations (1019) [1], tolerance of contaminants, and selectivity associated with the power of enzymes. It is for this reason that I have sought to introduce supramolecular approaches into my organocatalysis [2]. From thermodynamics, there are two components to catalysis: organization (entropic) and

Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane

• Zahra Noori,
• Miquel Solà,
• Clara Viñas,
• Francesc Teixidor and
• Jordi Poater

Beilstein J. Org. Chem. 2025, 21, 412–420, doi:10.3762/bjoc.21.29

• chemistry [4][5][6]. Pyrazoles are also extensively employed in agrochemicals, serving as key components in insecticides, herbicides, and fungicides [7]. Beyond their chemical uses, pyrazoles play an important role in the construction of supramolecular assemblies and molecular systems designed for