Synthesis and supramolecular self-assembly of glutamic acid-based squaramides

• Juan V. Alegre-Requena,
• Marleen Häring,
• Isaac G. Sonsona,
• Alex Abramov,
• Eugenia Marqués-López,
• Raquel P. Herrera and
• David Díaz Díaz

Beilstein J. Org. Chem. 2018, 14, 2065–2073, doi:10.3762/bjoc.14.180

• crystal engineering [13][14][15][16][17]. Despite their isosteric relationship with ureas, which have become key synthons in supramolecular chemistry [18][19], there are only a few reports on the formation of self-assembled supramolecular gels using squaramide derivatives [20][21][22][23]. Along this line

Coordination-driven self-assembly vs dynamic covalent chemistry: versatile methods for the synthesis of molecular metallarectangles

• Li-Li Ma,
• Jia-Qin Han,
• Wei-Guo Jia and
• Ying-Feng Han

Beilstein J. Org. Chem. 2018, 14, 2027–2034, doi:10.3762/bjoc.14.178

• self-assembly; dynamic covalent chemistry; half-sandwich rhodium complex; metallarectangles; one-pot reaction; supramolecular chemistry; Introduction Over the past two decades, supramolecular structures with organometallic half-sandwich fragments have attracted much attention, including

Rational design of boron-dipyrromethene (BODIPY) reporter dyes for cucurbit[7]uril

• Mohammad A. Alnajjar,
• Jürgen Bartelmeß,
• Robert Hein,
• Pichandi Ashokkumar,
• Mohamed Nilam,
• Werner M. Nau,
• Knut Rurack and
• Andreas Hennig

Beilstein J. Org. Chem. 2018, 14, 1961–1971, doi:10.3762/bjoc.14.171

• transfer; supramolecular chemistry; Introduction Cucurbit[n]urils (CBn, n = 5–8, 10, and 14) are a class of macrocyclic host molecules which are water soluble, nontoxic, and are able to bind a large variety of neutral and cationic guests in their inner cavity with high affinity [1][2][3][4]. This unique

• materials science, but its use in supramolecular chemistry is so far very rare [60][61][62][63][64]. It can be applied to investigate translational and rotational diffusion of supramolecules as well as exchange kinetics. To demonstrate the compatibility of the new BODIPY dyes with FCS, we have determined

Synthesis and characterization of π–extended “earring” subporphyrins

• Haiyan Guan,
• Mingbo Zhou,
• Bangshao Yin,
• Ling Xu and
• Jianxin Song

Beilstein J. Org. Chem. 2018, 14, 1956–1960, doi:10.3762/bjoc.14.170

• 3Pd is further red-shifted and more intense. Keywords: aromaticity; earring subporphyrin; π-extended; supramolecular chemistry; Findings Since its first synthesis in 2006 [1][2], subporphyrin, the lowest homolog of porphyrins, has received considerable attention [3][4][5][6][7][8] due to its 14π

Recent advances in materials for organic light emitting diodes

• Eli Zysman-Colman

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

• obtained his Ph.D. from McGill University in 2003. He then completed two postdoctoral fellowships, one in supramolecular chemistry at the Organic Chemistry Institute, University of Zurich and the other in inorganic materials chemistry at Princeton University. After beginning his career in Canada, he moved

Strong binding and fluorescence sensing of bisphosphonates by guanidinium-modified calix[5]arene

• Jie Gao,
• Zhe Zheng,
• Lin Shi,
• Si-Qi Wu,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2018, 14, 1840–1845, doi:10.3762/bjoc.14.157

• in view of low cost, ease of use and high sensitivity of optical sensing modalities, but remains a challenge since BPs are considered as unlabeled analytes. With the development of the host–guest concept in supramolecular chemistry, the indicator displacement assay (IDA), pioneered by Prof. Anslyn

Synthesis of diamido-bridged bis-pillar[5]arenes and tris-pillar[5]arenes for construction of unique [1]rotaxanes and bis-[1]rotaxanes

• Ying Han,
• Li-Ming Xu,
• Cui-Yun Nie,
• Shuo Jiang,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2018, 14, 1660–1667, doi:10.3762/bjoc.14.142

• mechanically interlocked molecules, but also developed the potential applications of pillar[5]arene in supramolecular chemistry. The design and construction of diverse mechanically interlocked molecules are underway in our laboratory. single crystal structure of pillar[5]arene 2a. Single crystal structure of

A conformationally adaptive macrocycle: conformational complexity and host–guest chemistry of zorb[4]arene

• Liu-Pan Yang,
• Song-Bo Lu,
• Arto Valkonen,
• Fangfang Pan,
• Kari Rissanen and
• Wei Jiang

Beilstein J. Org. Chem. 2018, 14, 1570–1577, doi:10.3762/bjoc.14.134

• binding behavior of ZB4 and lays the basis for the construction of stimuli-responsive materials with ZB4 as a major component. Keywords: conformations; host–guest chemistry; macrocycles; supramolecular chemistry; zorb[4]arene; Introduction Macrocyclic receptors are the principal workhorses used in

• supramolecular chemistry [1]. A myriad of synthetic macrocycles have sprouted during the past decade, greatly enriching the arsenal of supramolecular chemists [2][3][4][5][6][7][8][9][10][11]. The majority of artificial macrocycles are featured with rigid backbones as it is widely accepted that preorganization

Hyper-reticulated calixarene polymers: a new example of entirely synthetic nanosponge materials

• Alberto Spinella,
• Marco Russo,
• Antonella Di Vincenzo,
• Delia Chillura Martino and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2018, 14, 1498–1507, doi:10.3762/bjoc.14.127

• ; solid-state NMR; Introduction Nanosponges (NSs) [1][2][3] constitute an emerging area of both materials chemistry and supramolecular chemistry due to their peculiar properties, which have been object of an increasing interest during the last years. These materials are constituted by hyper-reticulated

Recent applications of chiral calixarenes in asymmetric catalysis

• Mustafa Durmaz,
• Erkan Halay and
• Selahattin Bozkurt

Beilstein J. Org. Chem. 2018, 14, 1389–1412, doi:10.3762/bjoc.14.117

• calixarene; organocatalyst; supramolecular catalyst; Introduction The catalysis of organic reactions by macrocyclic host compounds is a longstanding proposed application of supramolecular chemistry and utilizes the use of noncovalent interactions in catalytic systems to achieve higher reaction rates, more

Binding abilities of polyaminocyclodextrins: polarimetric investigations and biological assays

• Marco Russo,
• Daniele La Corte,
• Annalisa Pisciotta,
• Serena Riela,
• Rosa Alduina and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2751–2763, doi:10.3762/bjoc.13.271

• our materials to exploit both the cavity and the polycationic branches, thus functioning as bimodal ligands. Keywords: aminocyclodextrins; binding properties; nitroanilines; pDNA; polarimetry; supramolecular chemistry; Introduction Polyamine macromolecules have attracted a widespread interest for

Binding abilities of a chiral calix[4]resorcinarene: a polarimetric investigation on a complex case of study

• Marco Russo and
• Paolo Lo Meo

Beilstein J. Org. Chem. 2017, 13, 2698–2709, doi:10.3762/bjoc.13.268

• : calix[4]resorcinarene; host–guest complexes; p-nitroanilines; polarimetry; supramolecular chemistry; Introduction During the last decades calix[n]arenes and calix[n]resorcinarenes (CAs) have emerged as versatile supramolecular host systems for various applications [1][2][3][4][5], spanning from sensors

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• field of supramolecular chemistry [27][28][29], for solvent-free preparation of co-crystals, and adducts [30][31][32][33][34][35][36][37][38], polymorphs [12], supramolecular aggregates [4][30][39][40][41][42], host–guest complexes [5][43][44][45], metal-organic frameworks (MOFs) [8][28][44][46][47][48

• ][49][50], and coordination networks [46][47][48][51]. All these applications comprise the formation of intermolecular interactions, the basis of supramolecular chemistry. This discipline was fully recognized internationally with the attribution of the Nobel Prize of Chemistry in 1987 to Donald J. Cram

• further biomedical/pharmaceutical applications [71], such as cancer therapy [81][82][83]. MOFs combine coordination and supramolecular chemistry. Coordination chemistry is present in the coordination of organic molecules (linkers) to metal ions or clusters (coordination centers), while supramolecular

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• ; pemetrexed; supramolecular chemistry; Introduction Herein, supramolecular host–guest complexes of the potent folic acid inhibitor pemetrexed (PTX, Figure 1a) with native cyclodextrins (α-, β- and γ-CDs, Figure 1b) in the gas phase (MS), in solution (NMR, UV–vis) and in the solid state (Raman, FTIR–ATR) were

Superstructures with cyclodextrins: Chemistry and applications IV

• Gerhard Wenz

Beilstein J. Org. Chem. 2017, 13, 2157–2159, doi:10.3762/bjoc.13.215

• are well-suited for the design of molecular machines, which were the subject of the 2016 Nobel Prize in Chemistry [8][9]. Since superstructures are accessible through rational design, supramolecular chemistry had a great influence on organic and macromolecular chemistry as well as pharmacology and

Mechanically induced oxidation of alcohols to aldehydes and ketones in ambient air: Revisiting TEMPO-assisted oxidations

• Andrea Porcheddu,
• Evelina Colacino,
• Giancarlo Cravotto,
• Francesco Delogu and
• Lidia De Luca

Beilstein J. Org. Chem. 2017, 13, 2049–2055, doi:10.3762/bjoc.13.202

• aims to provide alternative methods to traditional syntheses in organic and inorganic chemistry [49][60][61]. Mechanochemistry is also used in supramolecular chemistry [62] and metal-organic chemistry [63]. In this work, we show that mechanical processing by ball milling can represent a viable solution

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• materials like stainless steel, tungsten carbide, zirconia, agate, etc. [24]. In the past decade, mechanochemical reactions were developed under the areas of chemistry like supramolecular chemistry [25][26], organic synthesis [27][28], nanoparticle synthesis, etc. [29][30]. The historical development of

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• gives access to diverse chemical structures which could be considered for further studies, e.g., the biological activity of the triazole-based compounds and the use of threefold symmetrically substituted triaminoguanidines as novel hosts in supramolecular chemistry or as ligands in coordination

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

• Nikolay V. Lukashev,
• Gennadii A. Grabovyi,
• Dmitry A. Erzunov,
• Alexey V. Kazantsev,
• Gennadij V. Latyshev,
• Alexei D. Averin and
• Irina P. Beletskaya.

Beilstein J. Org. Chem. 2017, 13, 564–570, doi:10.3762/bjoc.13.55

• template for design of complex molecules has become increasingly popular in pharmacology, supramolecular chemistry and nanoscience over recent years [4][5]. Many macrocyclic dimeric derivatives of bile acid were described [6][7][8]. As a rule, a route to the majority of macrocyclic structures requires

Spectral and DFT studies of anion bound organic receptors: Time dependent studies and logic gate applications

• Srikala Pangannaya,
• Neethu Padinchare Purayil,
• Shweta Dabhi,
• Venu Mankad,
• Prafulla K. Jha,
• Satyam Shinde and
• Darshak R. Trivedi

Beilstein J. Org. Chem. 2017, 13, 222–238, doi:10.3762/bjoc.13.25

• Srikala Pangannaya Neethu Padinchare Purayil Shweta Dabhi Venu Mankad Prafulla K. Jha Satyam Shinde Darshak R. Trivedi Supramolecular Chemistry Laboratory, Department of Chemistry, National Institute of Technology Karnataka (NITK), Surathkal, India Department of Physics, Maharaja

Efficient access to β-vinylporphyrin derivatives via palladium cross coupling of β-bromoporphyrins with N-tosylhydrazones

• Vinicius R. Campos,
• Ana T. P. C. Gomes,
• Anna C. Cunha,
• Maria da Graça P. M. S. Neves,
• Vitor F. Ferreira and
• José A. S. Cavaleiro

Beilstein J. Org. Chem. 2017, 13, 195–202, doi:10.3762/bjoc.13.22

• fields, including medicine [1][2][3] , supramolecular chemistry [4][5][6] and catalysis [7][8][9][10]; their functionalization became a target for several research groups [11][12][13]. In particular, the insertion of functional groups into the macrocyclic core merits considerable attention due to the

Diastereoselective anodic hetero- and homo-coupling of menthol-, 8-methylmenthol- and 8-phenylmenthol-2-alkylmalonates

• Matthias C. Letzel,
• Hans J. Schäfer and
• Roland Fröhlich

Beilstein J. Org. Chem. 2017, 13, 33–42, doi:10.3762/bjoc.13.5

• as a chiral auxiliary [27] to control the stereochemistry in Diels–Alder reactions [28], [2 + 2]- and [3 + 2]-cycloadditions and asymmetric ene reactions [29]; furthermore, it has been applied in 1,4-cuprate additions [30], Grignard additions [31], in supramolecular chemistry [32] and in alkylation

New approaches to organocatalysis based on C–H and C–X bonding for electrophilic substrate activation

• Pavel Nagorny and
• Zhankui Sun

Beilstein J. Org. Chem. 2016, 12, 2834–2848, doi:10.3762/bjoc.12.283

• the near future. Electrophile Activation by Hydrogen Bond Donors [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Early examples of C–H hydrogen bonds and their recent use in supramolecular chemistry [18][19][32][33][34]. Design of 1,2,3-triazole-based catalysts for trityl group transfer

• proposed the formation of a C–H hydrogen bond between chloroform and ethereal solvents in 1935 [18], and Lipscomb discovered hydrogen bonding in solid hydrogen cyanide in 1951 [19], until recently C–H hydrogen bonds have been mostly observed in the solid state (Figure 2). Recent studies in supramolecular

• chemistry have demonstrated that hydrogen bonds formed by C–H bonds are not necessarily “weak”, and in certain cases are almost as strong as more traditional A–H···A bonds [20]. The C–H hydrogen bonding between the substrate and the catalyst could be of great significance for transition state organization

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• integrated with functional fragments upon coordination with metals can undergo significant changes in molecular shape and aggregation state that can be used in the design of smart adaptive materials [1][2]. Some important bis- and trishydrazone ligands used in catalysis, coordination and supramolecular

• chemistry are shown in Figure 1. Despite complex and sophisticated polyhydrazone ligands have been designed in the last decade, more structurally simple poly(hydrazonomethyl)amines of type I (Scheme 1), which are analogs of well-known poly(oximinomethyl)amine and poly(azolylmethyl)amine ligands [18][19][20

Experimental and theoretical investigations into the stability of cyclic aminals

• Edgar Sawatzky,
• Antonios Drakopoulos,
• Martin Rölz,
• Christoph Sotriffer,
• Bernd Engels and
• Michael Decker

Beilstein J. Org. Chem. 2016, 12, 2280–2292, doi:10.3762/bjoc.12.221

• Tetraponera sp. [1][2]. It is also present in ligands of ruthenium-based catalysts for metathesis [3], in imidazolidines acting as antiprotozoal and antibacterial agents [4][5], in Tröger’s base derivatives with diverse applications [6][7][8][9][10][11][12][13][14] (e.g., asymmetric catalysis, supramolecular

• chemistry, DNA intercalation, etc.) or in synthetic tetrahydroquinazolines as cholinesterase (ChE) inhibitors [15][16][17] as well as ChE inhibitors based on the scaffold of the naturally occurring alkaloid physostigmine from the calabar bean physostigma venenosum [18][19] (Figure 1). This is just a small