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

• 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

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

• 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

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

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

• polarization (enthalpic) (Figure 1). Organization, the control of the position(s) and orientation(s) of reacting molecules, has been achieved historically in supramolecular chemistry using “pre-organized” catalyst designs (vide infra). More recently, organization has been mooted by List as a unifying concept

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

• materials. Keywords: hydrogen-bonded macrocycle; orthogonal self-assembly; shape-persistent; supramolecular polymer; Introduction Host–guest interactions, particularly those involving macrocycles as hosts [1], have found a myriad of applications in supramolecular chemistry [2][3][4] owing to their ability

• that by applying the design rules commonly known for metallosupramolecular polymers and macrocycle-mediated dimerization to supramolecular chemistry, we would be able to generate supramolecular polymers with this heterodifunctional monomer, with one end comprising two macrocycles and the other end

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

• glutamate); polysarcosine; shape transformation; stomatocyte; supramolecular chemistry; Introduction Polymeric vesicles represent a promising candidate for usage in drug delivery systems due to their facile assembly and ability to provide a stable soft interface. Among these materials, polyethylene glycol

Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[j]fluoranthenes via a Pd-catalyzed Suzuki–Miyaura/C–H arylation cascade

• Merve Yence,
• Dilgam Ahmadli,
• Damla Surmeli,
• Umut Mert Karacaoğlu,
• Sujit Pal and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2024, 20, 3290–3298, doi:10.3762/bjoc.20.273

• focus of extensive research within the past two decades due to their interesting structural features, attractive photophysical properties, and diverse applications [2]. Indeed, fluoranthenes are particularly useful in supramolecular chemistry, organic electronics, and materials science [3] as

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

• Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

• , porphyrins and corroles, which are structurally related to porphyrins. Calix[4]pyrroles are versatile receptors in supramolecular chemistry while porphyrins are considered as ‘pigment of life’ due to their role in vital biological processes. Beyond their natural functions, synthetic porphyrins have been

• conformational flexibility, allowing them to adopt four key conformations: 1,3-alternate, cone, partial cone, and 1,2-alternate [1][2]. Calix[4]pyrroles are one of the most studied hosts in supramolecular chemistry, finding use in applications of molecular recognition and extraction, drug delivery, ion transport

• metal-free porphyrins. 1.1 Calix[4]pyrrole macrocycles as organocatalysts Calix[4]pyrroles act as versatile ligands in supramolecular chemistry and have been widely studied as binding hosts for various guests such as anions, ion pairs, or neutral compounds [4][30][31], ligands for p-block elements, as

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

• ], Szumna [37][38][39], Reinhoudt [40][41], Konishi [42][43][44], Tiefenbacher [45][46][47][48][49][50][51][52], Strongin [53][54][55] among others. The wide-ranging popularity of resorcin[n]arenes is rooted in the numerous applications these compounds have in supramolecular chemistry, e.g., catalysis and

• reported herein may impact the synthesis of other macrocyclic arene species, e.g., calix[n]arenes, calix[4]pyrroles, pillar[n]arenes, and cucurbit[n]urils [90][91][92]. Perspective Supramolecular chemistry is a mature field that has crossed boundaries into many other scientific areas. However, the work

Synthesis and conformational analysis of pyran inter-halide analogues of ᴅ-talose

• Olivier Lessard,
• Mathilde Grosset-Magagne,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2024, 20, 2442–2454, doi:10.3762/bjoc.20.208

• , this study should be of general interest in the understanding of weak interactions that are now important to so many areas of chemistry, such as crystal engineering and supramolecular chemistry. Synthesis of trihalogenated pyrans: a) Chiron approach to multivicinal inter-halide derived from

Novel truxene-based dipyrromethanes (DPMs): synthesis, spectroscopic characterization and photophysical properties

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2024, 20, 2163–2170, doi:10.3762/bjoc.20.186

• potential applications in the arena of supramolecular chemistry in general, sensing, molecular recognition and self-assembly in particular in has yet to be explored. Moreover, applications of the truxene derivatives in catalysis are also scared, and needs to be advanced in future research. Experimental

Harnessing the versatility of hydrazones through electrosynthetic oxidative transformations

• Aurélie Claraz

Beilstein J. Org. Chem. 2024, 20, 1988–2004, doi:10.3762/bjoc.20.175

• ; Introduction Hydrazones represent an important class of organic compounds. They can be readily prepared through the condensation of hydrazine derivatives with aldehydes or ketones. They have found widespread applications in materials sciences and supramolecular chemistry [1][2][3][4][5]. Importantly, they are

Switchable molecular tweezers: design and applications

• Pablo Msellem,
• Maksym Dekthiarenko,
• Nihal Hadj Seyd and
• Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

• the tweezers to selectively bind aromatic guests within a cavity, utilizing an induced fit mechanism. Subsequently, with the emergence and advancement of supramolecular chemistry, the field of molecular tweezers experienced rapid expansion, witnessing the development of rigid clips by Klärner [2] and

• explore their applications in various domains. Switchable molecular tweezers as an emerging direction in supramolecular chemistry Among the large variety of molecular machines capable of controlling mechanical motion in response to stimuli, we found switchable molecular tweezers particularly appealing

• first part will be devoted to chemically responsive tweezers, including stimuli such as pH, metal coordination, and anion binding. Then, redox-active and photochemical tweezers will be presented. Keywords: coordination; molecular recognition; molecular switches; photoswitch; redox; supramolecular

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

• Christina Schøttler,
• Kasper Lund-Rasmussen,
• Line Broløs,
• Philip Vinterberg,
• Ema Bazikova,
• Viktor B. R. Pedersen and
• Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

• Tetrathiafulvalene (TTF, Figure 1) is a redox-active molecule that has been widely explored in materials chemistry and supramolecular chemistry [1][2][3][4][5][6][7][8]. TTF reversibly undergoes two sequential one-electron oxidations, generating first a radical cation (TTF+•) and subsequently a dication (TTF2

Substituent-controlled construction of A₄B₂-hexaphyrins and A₃B-porphyrins: a mechanistic evaluation

• Seda Cinar,
• Dilek Isik Tasgin and
• Canan Unaleroglu

Beilstein J. Org. Chem. 2023, 19, 1832–1840, doi:10.3762/bjoc.19.135

• of porphyrinogen and hexaphyrinogen forms. Keywords: A4B2-hexaphyrin; A3B-porphyrin; N-tosylimine; Cu(OTf)2 catalysis; HRESI–TOF analysis; Introduction Porphyrins and expanded porphyrins have found widespread applications in supramolecular chemistry [1][2][3][4]. Expanded porphyrins are utilized as

Active-metal template clipping synthesis of novel [2]rotaxanes

• Cătălin C. Anghel,
• Teodor A. Cucuiet,
• Niculina D. Hădade and
• Ion Grosu

Beilstein J. Org. Chem. 2023, 19, 1776–1784, doi:10.3762/bjoc.19.130

• ; Department of Organic Chemistry, Biochemistry and Catalysis, Research Centre of Applied Organic Chemistry, 90-92 Panduri Street, RO-050663 Bucharest, Romania 10.3762/bjoc.19.130 Abstract Mechanically interlocked molecules (MIMs) have been important synthetic targets in supramolecular chemistry due to their

• in 2016. While initially obtained as chemical curiosities, rotaxanes offer now exciting opportunities for scientific advancements in supramolecular chemistry and applications in various fields ranging from molecular machines and switches [4][5][6][7][8][9] to catalysis [10][11], molecular electronics

Effects of the aldehyde-derived ring substituent on the properties of two new bioinspired trimethoxybenzoylhydrazones: methyl vs nitro groups

• Dayanne Martins,
• Roberta Lamosa,
• Talis Uelisson da Silva,
• Carolina B. P. Ligiero,
• Sérgio de Paula Machado,
• Daphne S. Cukierman and
• Nicolás A. Rey

Beilstein J. Org. Chem. 2023, 19, 1713–1727, doi:10.3762/bjoc.19.125

• around the conjugated amide single bond (N–C=O). N-Acylhydrazones have also gained attention in literature due to other applications, ranging from medicine to supramolecular chemistry [7][8]. Among their applicability is the area of optoelectronic devices, in which they are used for the manufacture of

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

• the possible future directions. Keywords: crown ethers; porphyrinoids; self-assembly; sensors; supramolecular chemistry; Introduction Many areas of modern supramolecular chemistry, organic, inorganic, materials and coordination chemistry, are based upon macrocyclic compounds of specifically-designed

• structures and tailored functions [1][2][3]. The design of novel macrocyclic compounds has laid the ground for phenomenal developments constituting supramolecular chemistry as a branch of chemical sciences. These fundamental developments included the discovery of crown ethers by Pedersen [4], followed by the

• the development of various areas of supramolecular chemistry. Porphyrins and crown ethers continue to play a significant role in these studies. As a result of combining structural motifs from both classes of archetypal macrocyclic compounds, a series of fascinating molecular objects representing

Complexes of resorcin[4]arene with secondary amines: synthesis, solvent influence on “in-out” structure, and theoretical calculations of non-covalent interactions

• Waldemar Iwanek

Beilstein J. Org. Chem. 2023, 19, 1525–1536, doi:10.3762/bjoc.19.109

• exchange and dispersion interactions in CHCl3 in relation to DMSO are the driving forces behind the placement of sec-amine molecules into the R[4]A cavity and the formation of “in” type complexes. Keywords: complexes; DFT calculations; hydrogen bond; resorcin[4]arene; supramolecular chemistry

• ], amino alcohols [10], and amino acids [11] have been studied due to their potential applications in supramolecular chemistry, drug delivery, and molecular recognition. The complexation of R[4]A with amines is based on the formation of hydrogen bonds between the hydroxy groups of the resorcinol units and

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• discovery of the copper-catalyzed alkyne azide (3 + 2) cycloaddition (CuAAC) [3][4], has dramatically changed the approaches to many problems in chemistry, supramolecular chemistry, materials science, biological chemistry and related fields (selected reviews: [5][6][7][8][9][10][11][12][13][14][15

Exploring the role of halogen bonding in iodonium ylides: insights into unexpected reactivity and reaction control

• Carlee A. Montgomery and
• Graham K. Murphy

Beilstein J. Org. Chem. 2023, 19, 1171–1190, doi:10.3762/bjoc.19.86

• numerous similar attributes, halogen bonding has also proven to be a viable alternative in methodologies that rely on hydrogen bond initiation. For example, both halogen- and hydrogen bonding can be used in supramolecular chemistry as the binding mechanism in photoresponsive receptors [73][74][75][76][77

A fluorescent probe for detection of Hg²⁺ ions constructed by tetramethyl cucurbit[6]uril and 1,2-bis(4-pyridyl)ethene

• Xiaoqian Chen,
• Naqin Yang,
• Yue Ma,
• Xinan Yang and
• Peihua Ma

Beilstein J. Org. Chem. 2023, 19, 864–872, doi:10.3762/bjoc.19.63

• Xiaoqian Chen Naqin Yang Yue Ma Xinan Yang Peihua Ma Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China Guiyang College of Humanities and Science, Guiyang 550025, China 10.3762/bjoc.19.63 Abstract In this paper, tetramethyl

• form various host–guest inclusion complexes [16][17][18][19][20], which have broad application prospects in supramolecular catalysis [21][22][23], molecular recognition [24][25], and drug delivery [26][27]. In recent years, in the field of supramolecular chemistry, the detection of analytes based on