[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

• Margareta Sohora,
• Leo Mandić and
• Nikola Basarić

Beilstein J. Org. Chem. 2020, 16, 1296–1304, doi:10.3762/bjoc.16.110

• achieved by use of supramolecular chemistry [36][37]. For example, stereoselectivity has been reported for photochemical reactions taking place in the inclusion complexes with CD [38][39][40][41] or structurally modified CDs [42][43][44][45][46][47]. Since β-CD is often used in pharmaceutical applications

Exploring the scope of DBU-promoted amidations of 7-methoxycarbonylpterin

• Anna R. Bockman and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2020, 16, 509–514, doi:10.3762/bjoc.16.46

• attractive scaffold in the field of supramolecular chemistry, due to their well-defined donor/acceptor hydrogen-bonding arrays [10][11]. One limitation often encountered with the synthesis of structurally diverse pterins is the notorious insolubility in most solvents. This can be dealt with by preemptive

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• ], diiodoacetylene [15] and iodo/bromoethynyl moieties [16] have revealed that the XB-donors interacting with XB-acceptors (a nucleophilic region) are in approximately linear orientation. Besides, linearity, tunability and hydrophobicity (features of the XB ) are widely applied in crystal engineering, supramolecular

• chemistry, anion recognition, organocatalysis, materials science and tuning of biomolecular systems [17][18][19][20][21][22][23][24][25][26][27]. 1,2,3-Triazole-based XB-donors, such as 5-iodo-1,2,3-triazoles A [28][29][30][31][32][33] and 5-iodo-1,2,3-triazolium B [34][35][36][37] (Figure 1), are promising

The interaction between cucurbit[8]uril and baicalein and the effect on baicalein properties

• Xiaodong Zhang,
• Jun Xie,
• Zhiling Xu,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 71–77, doi:10.3762/bjoc.16.9

• Xiaodong Zhang Jun Xie Zhiling Xu Zhu Tao Qianjun Zhang Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China 10.3762/bjoc.16.9 Abstract The host–guest interactions between baicalein (BALE) and cucurbit[8]uril (Q[8]) and the

A chiral self-sorting photoresponsive coordination cage based on overcrowded alkenes

• Constantin Stuckhardt,
• Diederik Roke,
• Wojciech Danowski,
• Edwin Otten,
• Sander J. Wezenberg and
• Ben L. Feringa

Beilstein J. Org. Chem. 2019, 15, 2767–2773, doi:10.3762/bjoc.15.268

• rotation upon irradiation with light [38][39][40]. Moreover, they can be used as chiroptical multistate switches to control various functions in areas such as catalysis [41][42][43], soft materials [43][44][45] and supramolecular chemistry [46][47]. Employing molecular motors as ligands in SCCs provides an

A combinatorial approach to improving the performance of azoarene photoswitches

• Joaquin Calbo,
• Aditya R. Thawani,
• Rosina S. L. Gibson,
• Andrew J. P. White and
• Matthew J. Fuchter

Beilstein J. Org. Chem. 2019, 15, 2753–2764, doi:10.3762/bjoc.15.266

• including imaging applications [20], photopharmacology [21], supramolecular chemistry [22][23], responsive foams [24], coordination chemistry [25] and DNA nanotechnology [26][27]. Whilst the azopyrazoles have excellent properties for use in a variety of photo-addressable applications, it remains frustrating

• -fluoroazopyrazole as part of their study of the supramolecular chemistry of these systems. Irradiating their compound at 365 nm enables near quantitative E→Z conversion, however, the 520 nm PSS provides 55% of the E-isomer. In water, this compound possesses a thermal half-life of >11 days. Herein, we present

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• of conjugated diynes (DYCM) is promoted by the benzylidyne tungsten complex II with silanolate ligands (X = OSi(Ot-Bu)3) [21][22]; this catalyst is also active in classical alkyne metathesis [23]. Complex III with chelating phenoxide ligands [24][25][26][27] is mostly applied in supramolecular

• chemistry [28][29][30][31][32], used for instance in the preparation of aryleneethynylene macrocycles and cages through alkyne metathesis [33][34][35][36][37][38][39]. Additionally, already since the 1980s the influence of fluorinated and unfluorinated alkoxide ligands has been widely investigated [40][41

Anion-driven encapsulation of cationic guests inside pyridine[4]arene dimers

• Anniina Kiesilä,
• Jani O. Moilanen,
• Anneli Kruve,
• Christoph A. Schalley,
• Perdita Barran and
• Elina Kalenius

Beilstein J. Org. Chem. 2019, 15, 2486–2492, doi:10.3762/bjoc.15.241

• vital importance to understand the supramolecular chemistry of pyridinearenes. Interestingly, ternary complexes of 12 containing both cation and solvent are not observed in either of the ESI-MS modes, even though in earlier studies such complexes were observed with solvent and anion [11]. This points to

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• macrocycles and focus on their application in different areas of supramolecular chemistry. The synthesis is mostly relying on the well-known “click reaction” (CuAAC) leading to 1,4-disubstituted 1,2,3-triazoles that then can be quaternized. Applications of triazolium macrocycles thus prepared include

• -triazolium macrocycles; Review 1. Introduction Supramolecular chemistry – “The chemistry beyond the molecule” [1] – is an ever growing interdisciplinary area has emerged from the early host–guest chemistry to more elaborate bio-inspired supramolecular aggregates by exploiting various noncovalent

• critical role of negatively charged species in numerous biological, environmental, chemical and medicinal processes, anion receptors and transporters play an important role in supramolecular chemistry [17][29]. Thus, diverse anion receptors based on 1,2,3-triazolium recognition elements have been reported

Multiple threading of a triple-calix[6]arene host

• Veronica Iuliano,
• Roberta Ciao,
• Emanuele Vignola,
• Carmen Talotta,
• Patrizia Iannece,
• Margherita De Rosa,
• Annunziata Soriente,
• Carmine Gaeta and
• Placido Neri

Beilstein J. Org. Chem. 2019, 15, 2092–2104, doi:10.3762/bjoc.15.207

• Veronica Iuliano Roberta Ciao Emanuele Vignola Carmen Talotta Patrizia Iannece Margherita De Rosa Annunziata Soriente Carmine Gaeta Placido Neri Laboratory of Supramolecular Chemistry, Dipartimento di Chimica e Biologia " A. Zambelli", Università di Salerno, Via Giovanni Paolo II 132, 84084

• stereoselective formation of endo-alkyl pseudo[n]rotaxane stereoisomers. Keywords: calixarene; multiple-threading; pseudo[n]rotaxane; stereoisomers; Introduction The self-assembly [1] of smaller components to larger aggregates represents one of the most spectacular phenomena in supramolecular chemistry [2][3][4

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• ]tetrazines a useful macrocyclic platform for the study of supramolecular chemistry. Applications of the phthalimide-containing functionalized O6-corona[3]arene[3]tetrazines are being actively perused and results will be reported in due course. Experimental General procedure for the synthesis of 3a–e. To a

Complexation of chiral amines by resorcin[4]arene sulfonic acids in polar media – circular dichroism and diffusion studies of chirality transfer and solvent dependence

• Bartosz Setner and
• Agnieszka Szumna

Beilstein J. Org. Chem. 2019, 15, 1913–1924, doi:10.3762/bjoc.15.187

• ; supramolecular chemistry; Introduction Despite of the great progress that has been made in supramolecular chemistry in polar and aqueous media, formation of discrete ordered supramolecular associates with precise patterns of noncovalent interactions still presents a challenge [1][2]. Especially self-assembly

• Bartosz Setner Agnieszka Szumna Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland 10.3762/bjoc.15.187 Abstract Directional self‐assembly of conformationally well-defined complexes in polar environment is still a major challenge in supramolecular

• chemistry. In the present study we demonstrate that resorcin[4]arene sulfonic acid (RSA) interacts with chiral amines (amino acid derivatives and aminocavitands) to form inclusion complexes and capsules based on electrostatic interactions. The complexes were characterized by circular dichroism and DOSY NMR

Novel macrocycles – and old ones doing new tricks

• Wei Jiang and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2019, 15, 1838–1839, doi:10.3762/bjoc.15.178

• 10.3762/bjoc.15.178 Keywords: macrocycles; supramolecular chemistry; Macrocycles [1] are the workhorses in supramolecular chemistry. Many basic supramolecular concepts have been developed through studying crown ethers, cryptands, podands and spherands in the 1970s and 1980s. For these contributions

• , macrocycles played a central role for the fundamental science that established supramolecular chemistry as an independent field of chemical research as well as for its applications in contemporary research on functional supramolecules and materials. Nowadays, the use of macrocycles has significantly

Complexation of 2,6-helic[6]arene and its derivatives with 1,1′-dimethyl-4,4′-bipyridinium salts and protonated 4,4'-bipyridinium salts: an acid–base controllable complexation

• Jing Li,
• Qiang Shi,
• Ying Han and
• Chuan-Feng Chen

Beilstein J. Org. Chem. 2019, 15, 1795–1804, doi:10.3762/bjoc.15.173

• groups. They have exhibited wide potential applications in supramolecular chemistry [31][32][33][34][35][36] for their unique structures and electron-rich cavities. In this paper, we report the complexation between 2,6-helic[6]arene and its four derivatives with 1,1′-dimethyl-4,4′-bipyridinium and

Host–guest interactions in nor-seco-cucurbit[10]uril: novel guest-dependent molecular recognition and stereoisomerism

• Xiaodong Zhang,
• Wei Wu,
• Zhu Tao and
• Xin-Long Ni

Beilstein J. Org. Chem. 2019, 15, 1705–1711, doi:10.3762/bjoc.15.166

• Xiaodong Zhang Wei Wu Zhu Tao Xin-Long Ni Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang 550025, China 10.3762/bjoc.15.166 Abstract The unique monomer and excimer fluorescence emissions of pyrene were first exploited as distinctly

An azobenzene container showing a definite folding – synthesis and structural investigation

• Abdulselam Adam,
• Saber Mehrparvar and
• Gebhard Haberhauer

Beilstein J. Org. Chem. 2019, 15, 1534–1544, doi:10.3762/bjoc.15.156

• the high dispersion energy in the compact cis,cis-isomer. Keywords: azobenzene; macrocycles; molecular switch; Introduction In supramolecular chemistry rigid scaffolds are required to arrange different recognition units in predefined distances and spatial orientation to each other [1]. One example

• possible, should lead to containers which are due to their foldable feature promising candidates for applications in supramolecular chemistry. Experimental General remarks: All chemicals were reagent grade and were used as purchased. Reactions were monitored by TLC analysis with silica gel 60 F254 thin

• Abdulselam Adam Saber Mehrparvar Gebhard Haberhauer Institut für Organische Chemie, Universität Duisburg-Essen, Universitätsstr. 7, D-45117 Essen, Germany 10.3762/bjoc.15.156 Abstract The combination of photo-switchable units with macrocycles is a very interesting field in supramolecular

2,3-Dibutoxynaphthalene-based tetralactam macrocycles for recognizing precious metal chloride complexes

• Li-Li Wang,
• Yi-Kuan Tu,
• Huan Yao and
• Wei Jiang

Beilstein J. Org. Chem. 2019, 15, 1460–1467, doi:10.3762/bjoc.15.146

• –guest chemistry; macrocycles; molecular recognition; precious metal chloride complexes; Introduction Macrocyclic receptors are the major workhorses in supramolecular chemistry. Design and synthesis of new macrocyclic receptors with new properties is always attractive but is also challenging [1

Introduction of an isoxazoline unit to the β-position of porphyrin via regioselective 1,3-dipolar cycloaddition reaction

• Xiujun Liu,
• Xiang Ma and
• Yaqing Feng

Beilstein J. Org. Chem. 2019, 15, 1434–1440, doi:10.3762/bjoc.15.143

• enantiomers of 3a is present, which assembled to a dimeric structure with the fifth chelation of a Zn2+ ion by the carbonyl group of the other molecule. The self-dimerization property of 3a may be utilized in supramolecular chemistry [50][51][52][53]. Experimental 1: Porphyrin phosphonium salt 1 was prepared

Reversible end-to-end assembly of selectively functionalized gold nanorods by light-responsive arylazopyrazole–cyclodextrin interaction

• Maximilian Niehues,
• Patricia Tegeder and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2019, 15, 1407–1415, doi:10.3762/bjoc.15.140

• linker molecule (dAAP) led to light-responsive reversible self-assembly of AuNR in an end-to-end manner as depicted in Scheme 1 to open up a novel strategy for the design of hybrid nanomaterials by supramolecular chemistry. Results and Discussion The AuNR (length: 58 nm, width: 25 nm, aspect-ratio: 2.3

Complexation of a guanidinium-modified calixarene with diverse dyes and investigation of the corresponding photophysical response

• Yu-Ying Wang,
• Yong Kong,
• Zhe Zheng,
• Wen-Chao Geng,
• Zi-Yi Zhao,
• Hongwei Sun and
• Dong-Sheng Guo

Beilstein J. Org. Chem. 2019, 15, 1394–1406, doi:10.3762/bjoc.15.139

• -consuming syntheses. Alternatively, supramolecular chemistry provides a non-covalent approach to achieve fluorescence sensing [2]. An elegant supramolecular strategy, named indicator displacement assay (IDA), was established and popularized by Anslyn and co-workers (Scheme 1a) [3][4]. The complexation of a

Efficient resolution of racemic crown-shaped cyclotriveratrylene derivatives and isolation and characterization of the intermediate saddle isomer

• Sven Götz,
• Andreas Schneider and
• Arne Lützen

Beilstein J. Org. Chem. 2019, 15, 1339–1346, doi:10.3762/bjoc.15.133

• ; cyclotriveratrylenes; HPLC; macrocycles; racemization; saddle isomer; Introduction Cyclotriveratrylenes (CTVs) [1][2][3][4][5][6][7][8] are cyclic bowl-shaped molecules and belong to the most studied concave host molecules in supramolecular chemistry besides, e.g., calixarenes and resorcinarenes [9], cyclodextrins

Host–guest interactions between p-sulfonatocalix[4]arene and p-sulfonatothiacalix[4]arene and group IA, IIA and f-block metal cations: a DFT/SMD study

• Valya K. Nikolova,
• Cristina V. Kirkova,
• Silvia E. Angelova and
• Todor M. Dudev

Beilstein J. Org. Chem. 2019, 15, 1321–1330, doi:10.3762/bjoc.15.131

• formation reactions. Keywords: complex formation; DFT; group IA; IIA and f-block metal cations; macrocycles; p-sulfonatocalix[4]arene; p-sulfonatothiacalix[4]arene; Introduction If macrocycles are pillars of the supramolecular chemistry, then calixarenes (“calix” = vase + “arene”) are the 3rd pillar after

Bambusuril analogs based on alternating glycoluril and xylylene units

• Tomáš Lízal and
• Vladimír Šindelář

Beilstein J. Org. Chem. 2019, 15, 1268–1274, doi:10.3762/bjoc.15.124

• Tomas Lizal Vladimir Sindelar Department of Chemistry and RECETOX, Masaryk University, Kamenice 5, 625 00 Brno, Czech Republic 10.3762/bjoc.15.124 Abstract The glycoluril monomer is a popular building block in supramolecular chemistry as it is used for the synthesis of versatile host molecules

• ; supramolecular chemistry; Introduction Macrocycles consisting of urea building blocks play an important role in supramolecular chemistry [1]. Urea N–H motifs provide macrocycles with the ability to act as anion receptors due to the stabilizing effect of N–H···anion hydrogen bonding [2][3][4]. Furthermore, the

N-doped carbon dots covalently functionalized with pillar[5]arenes for Fe³⁺ sensing

• Jia Gao,
• Ming-Xue Wu,
• Dihua Dai,
• Zhi Cai,
• Yue Wang,
• Wenhui Fang,
• Yan Wang and
• Ying-Wei Yang

Beilstein J. Org. Chem. 2019, 15, 1262–1267, doi:10.3762/bjoc.15.123

• units, the newly constructed fluorescent CCDs could recognize Fe3+ with high selectivity. Therefore, such CCDs can potentially serve as a promising chemical sensor for Fe3+ ions. Keywords: chemical sensor; CN-dots; fluorescence; ion recognition; supramolecular chemistry; Findings Carbon dots (C-dots

• macrocyclic compounds, especially new macrocyclic arenes, have become one of the research hotspots in supramolecular chemistry [11][12][13][14]. Among them pillarenes as a relatively new family of pillar-shaped members discovered a decade ago have played a key role due to their unique conformations

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• supramolecular chemistry applications. Keywords: conjugation; heterocycles; macrocycles; multicomponent reactions; steroids; Review 1 Introduction The utilization of multicomponent reactions (MCRs) [1] for the derivatization of biomolecules has continuously grown over the last years. These diversity-oriented

• in the pursuit of medicinal and supramolecular chemistry applications. Despite some review articles have described selected examples of MCRs used to modify and to macrocyclize steroidal compounds [12][13], to our knowledge there is no review exclusively dedicated to covering the applications of MCRs