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

Self-assembly behaviors of perylene- and naphthalene-crown macrocycle conjugates in aqueous medium

• Xin Shen,
• Bo Li,
• Tiezheng Pan,
• Jianfeng Wu,
• Yangxin Wang,
• Jie Shang,
• Yan Ge,
• Lin Jin and
• Zhenhui Qi

Beilstein J. Org. Chem. 2019, 15, 1203–1209, doi:10.3762/bjoc.15.117

• -assemblies have been recognized as a type of exciting nanomaterials with tremendous potential for research and commercial applications [1][2][3][4][5][6]. Thanks to the development of supramolecular chemistry, the ordered structures could be obtained through programmed self-assembly coupled with covalent

• ][31][32]. Nowadays, as the research in supramolecular chemistry is expanding into the aqueous realm, a systematic understanding of the interaction relationship of supramolecular self-assemblies and aqueous medium is becoming increasingly important [33][34][35][36]. As the first generation of

Halogen bonding and host–guest chemistry between N-alkylammonium resorcinarene halides, diiodoperfluorobutane and neutral guests

• Fangfang Pan,
• Mohadeseh Dashti,
• Michael R. Reynolds,
• Kari Rissanen,
• John F. Trant and
• Ngong Kodiah Beyeh

Beilstein J. Org. Chem. 2019, 15, 947–954, doi:10.3762/bjoc.15.91

• supramolecular chemistry and materials science [1][2][3]. New systems both help us to better understand the nature and impetus behind the self-assembly of these fascinating systems, while also providing new materials that can provide the basis for a wide number of applications [4][5]. Halogen bonding (XB), as a

Mechanochemistry of supramolecules

• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2019, 15, 881–900, doi:10.3762/bjoc.15.86

• . Contrastingly, achieving syntheses through mechanochemical methods are generally time-saving, environmentally friendly and more economical. This review is written to shed some light on supramolecular chemistry and the synthesis of various supramolecules through mechanochemistry. Keywords: ball milling

• conditions through covalent approaches. By using common synthetic methodologies chemists are able to proficiently synthesize a variety of both natural and unnatural molecular scaffolds [4][5][6]. The era of supramolecular chemistry began with the introduction of coordination theory by Alfred Werner in 1893

• supramolecular chemistry are dynamic combinatorial chemistry [11], subcomponent self-assembly approach [12][13][14], and systems chemistry [15][16][17][18], etc. There also has been growing interest towards exploration of nontraditional energy sources like visible light [19][20], microwave [21], mechanochemical

Homo- and hetero-difunctionalized β-cyclodextrins: Short direct synthesis in gram scale and analysis of regiochemistry

• Gábor Benkovics,
• Mihály Bálint,
• Éva Fenyvesi,
• Erzsébet Varga,
• Szabolcs Béni,
• Konstantina Yannakopoulou and
• Milo Malanga

Beilstein J. Org. Chem. 2019, 15, 710–720, doi:10.3762/bjoc.15.66

• -difunctionalization; regioselectivity; Introduction Cyclodextrins (CDs) are cyclic oligomers of α-D-glucopyranose (Figure 1 illustrates the heptamer, β-CD) that have attracted worldwide interest in various fields of applied supramolecular chemistry due to their ability to form host–guest inclusion complexes [1]. A

LCST phase behavior of benzo-21-crown-7 with different alkyl chains

• Yan Deng,
• Xing Li,
• Qiao Zhang,
• Zheng Luo,
• Chengyou Han and
• Shengyi Dong

Beilstein J. Org. Chem. 2019, 15, 437–444, doi:10.3762/bjoc.15.38

• -crown-7, B21C7s) can effectively control the thermo-responsive properties. Keywords: crown ethers; hydrophobic units; lower critical solution temperature; LCST; thermo-responsiveness; supramolecular chemistry; Introduction The introduction of stimuli-responsiveness into artificial materials is vital

• behavior, is a type of thermo-responsiveness [14][15][16], which has gained much attention in supramolecular chemistry, because of its profound impact on the development of stimuli-sensitive supramolecular materials with controllable and/or programmable phase separation properties [17][18][19]. Though LCST

First synthesis of cryptands with sucrose scaffold

• Patrycja Sokołowska,
• Michał Kowalski and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2019, 15, 210–217, doi:10.3762/bjoc.15.20

• ’,4,4’-penta-O-benzylsucrose and 1’,2,3,3’,4,4’-hexa-O-benzylsucrose. Keywords: cryptands; macrocyclization; sucrose; Introduction The design and synthesis of macrocyclic receptors is one of the main challenges of supramolecular chemistry [1][2]. These artificial systems exhibit interesting properties

Calixazulenes: azulene-based calixarene analogues – an overview and recent supramolecular complexation studies

• Paris E. Georghiou,
• Shofiur Rahman,
• Abdullah Alodhayb,
• Hidetaka Nishimura,
• Jaehyun Lee,
• Atsushi Wakamiya and
• Lawrence T. Scott

Beilstein J. Org. Chem. 2018, 14, 2488–2494, doi:10.3762/bjoc.14.225

• investigated. Keywords: azulene; calixarenes; calixazulenes; supramolecular chemistry; tetraalkylammonium salts; Introduction Among the great variety of synthetic macrocyclic molecular receptors which have been reported, those that are referred to by their generic name “calixarene” loom large [1][2][3]. The

• ]azulene 3. To shed light on possible explanations for these findings, our attention was again directed to computational results derived from DFT calculations which are increasingly being commonly used in supramolecular chemistry. The ωB97xD functional [25] which combines the long range functional ωB97x

• , in light of recent developments in the facile syntheses of other functionalzed azulenes as reported by Narita et al. [34] the potential for further syntheses of hetero-functionalized calixazulenes and their supramolecular chemistry may be realized. Further studies by us on these intriguing

Coordination-driven self-assembly of discrete Ru₆–Pt₆ prismatic cages

• Aderonke Ajibola Adeyemo and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2018, 14, 2242–2249, doi:10.3762/bjoc.14.199

• supramolecular chemistry leading to the formation of a single major product. Keywords: arene–ruthenium(II); heterometallic cages; platinum metalloligand; self-assembly; supramolecular architectures; Introduction Coordination-driven self-assembly of discrete architectures has evolved as a unique protocol to

• –ruthenium(II) acceptor clips/building blocks have been extensively utilized in supramolecular chemistry because of their rigid directionality toward electron-rich donors due to their restricted coordination sites as a result of the fixed position of the p-cymene moiety [24][93][98][99][100][101][102][103

Synthesis of a water-soluble 2,2′-biphen[4]arene and its efficient complexation and sensitive fluorescence enhancement towards palmatine and berberine

• Xiayang Huang,
• Xinghua Zhang,
• Tianxin Qian,
• Junwei Ma,
• Lei Cui and
• Chunju Li

Beilstein J. Org. Chem. 2018, 14, 2236–2241, doi:10.3762/bjoc.14.198

• Xiayang Huang Xinghua Zhang Tianxin Qian Junwei Ma Lei Cui Chunju Li School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 100 Hai-Quan Road, Shanghai 201418, P. R. China Department of Chemistry, Center for Supramolecular Chemistry and Catalysis, Shanghai University

• , medicine, and environment. Cyclodextrins [1][2][3][4], cucurbiturils [5][6][7][8][9][10][11], and calixarenes [12][13][14][15][16][17][18][19][20] have been widely used in aqueous supramolecular chemistry. In the past ten years, the chemistry of pillar[n]arenes has developed very quickly because of their

Dynamic light scattering studies of the effects of salts on the diffusivity of cationic and anionic cavitands

• Anthony Wishard and
• Bruce C. Gibb

Beilstein J. Org. Chem. 2018, 14, 2212–2219, doi:10.3762/bjoc.14.195

• light scattering; Hofmeister effect; ion–ion interactions; water; Introduction Although all life on planet Earth depends on aqueous solutions, our understanding of aqueous supramolecular chemistry is limited. As a result, as Smith has eloquently pointed out [1], the effects of buffers and salts on

Tetrathiafulvalene – a redox-switchable building block to control motion in mechanically interlocked molecules

• Hendrik V. Schröder and
• Christoph A. Schalley

Beilstein J. Org. Chem. 2018, 14, 2163–2185, doi:10.3762/bjoc.14.190

• ; supramolecular chemistry; tetrathiafulvalene; Introduction Undoubtedly, the exploration of nature’s molecular machines in the last century led to a paradigm change of how we think about working and organization processes on the molecular level [1][2][3]. Inspired by the way how energy and concentration

• supramolecular chemistry [28] and for the construction of MIMs [29], the good π-donor properties of TTF are frequently used to template donor–acceptor complexes with π-electron deficient macrocycles. If TTF undergoes oxidation, the π-donating effect decreases, whereas the TTF2+ dication can be considered as a π

Evaluation of dispersion type metal···π arene interaction in arylbismuth compounds – an experimental and theoretical study

• Ana-Maria Preda,
• Małgorzata Krasowska,
• Lydia Wrobel,
• Philipp Kitschke,
• Phil C. Andrews,
• Jonathan G. MacLellan,
• Lutz Mertens,
• Marcus Korb,
• Tobias Rüffer,
• Heinrich Lang,
• Alexander A. Auer and
• Michael Mehring

Beilstein J. Org. Chem. 2018, 14, 2125–2145, doi:10.3762/bjoc.14.187

• applications in the field of supramolecular chemistry [10][11][12] and pharmacology are of interest [13][14][15]. Lately, several studies regarding the metal···π interactions in organometallic compounds of antimony and bismuth [16][17][18][19] have been reported including intramolecular [20][21][22] and

• interaction as one of the emerging intermolecular interactions that are of particular interest to coordination chemists with regard to supramolecular chemistry [12]. However, most reports on main group metal···π interactions are based on the description of the single crystal structures and lack a profound

Calix[6]arene-based atropoisomeric pseudo[2]rotaxanes

• Carmine Gaeta,
• Carmen Talotta and
• Placido Neri

Beilstein J. Org. Chem. 2018, 14, 2112–2124, doi:10.3762/bjoc.14.186

• bis(benzylalkylammonium) axle [19], where the stereoselective formation of the pseudo[3]rotaxane with endo-alkyl orientation VIII was observed [19]. Calixarene macrocycles [22] have found numerous applications in several areas of supramolecular chemistry, such as (bio)molecular recognition [23] and

A switchable [2]rotaxane with two active alkenyl groups

• Xiu-Li Zheng,
• Rong-Rong Tao,
• Rui-Rui Gu,
• Wen-Zhi Wang and
• Da-Hui Qu

Beilstein J. Org. Chem. 2018, 14, 2074–2081, doi:10.3762/bjoc.14.181

• polymers. Keywords: alkenyl bond; functional crown ether; stimuli-responsiveness; switchable rotaxane; Introduction Along with the development of supramolecular chemistry, much attention has been paid to the design and synthesis of novel and complicated mechanical interlocked molecules (MIMs) [1][2][3][4

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