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Search for "calixarenes" in Full Text gives 52 result(s) in Beilstein Journal of Organic Chemistry.

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

Graphical Abstract
  • two bipyridine-calixarene units linked by a flexible spacer (Figure 15a) [59]. In the non-complexed state, the system presents no cavity. But, when copper(I) is introduced, a complex is formed with the two bipyridine units bringing the two calixarenes close to each other and creating a cavity suitable
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Published 01 Mar 2024

Bioinspired tetraamino-bisthiourea chiral macrocycles in catalyzing decarboxylative Mannich reactions

  • Hao Guo,
  • Yu-Fei Ao,
  • De-Xian Wang and
  • Qi-Qiang Wang

Beilstein J. Org. Chem. 2022, 18, 486–496, doi:10.3762/bjoc.18.51

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  • ][10][11][12][13][14]. Among which, macrocyclic compounds have attracted extensive attentions due to their enzyme-mimicking cavity and preorganized binding sites [4][6][15][16]. Various macrocyclic compounds including the privileged scaffolds like cyclodextrins [17][18][19], calixarenes [20][21][22][23
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Published 02 May 2022

Site-selective reactions mediated by molecular containers

  • Rui Wang and
  • Yang Yu

Beilstein J. Org. Chem. 2022, 18, 309–324, doi:10.3762/bjoc.18.35

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  • mimicking the recognition and catalysis behavior of enzymes with designed and synthesized molecular containers such as cyclodextrins, cucurbiturils, calixarenes, and resorcinarenes, chemists try to tackle problems of traditional synthetic chemistry, including increase in reactivity, induction of selectivity
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Published 14 Mar 2022

Synthesis of a novel aminobenzene-containing hemicucurbituril and its fluorescence spectral properties with ions

  • Qingkai Zeng,
  • Qiumeng Long,
  • Jihong Lu,
  • Li Wang,
  • Yuting You,
  • Xiaoting Yuan,
  • Qianjun Zhang,
  • Qingmei Ge,
  • Hang Cong and
  • Mao Liu

Beilstein J. Org. Chem. 2021, 17, 2840–2847, doi:10.3762/bjoc.17.195

Graphical Abstract
  • Macrocycles with converging binding sites and functional groups hold a key position in supramolecular chemistry, which has been repeatedly confirmed by classic macrocyclic molecules, such as crown ethers, cyclodextrins, calixarenes, cucurbiturils and their homologues [1]. For the past decades, numerous
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Published 06 Dec 2021

Insight into functionalized-macrocycles-guided supramolecular photocatalysis

  • Minzan Zuo,
  • Krishnasamy Velmurugan,
  • Kaiya Wang,
  • Xueqi Tian and
  • Xiao-Yu Hu

Beilstein J. Org. Chem. 2021, 17, 139–155, doi:10.3762/bjoc.17.15

Graphical Abstract
  • , calixarenes, and pillararenes. This minireview not only summarizes the role that macrocycles play in photocatalytic reactions but also clarifies the photocatalytic mechanisms. Finally, the future research efforts and new pathways to apply macrocycles and supramolecular hybrid materials in photocatalysis are
  • supramolecular hosts (Figure 1); crown ethers (CEs), cyclodextrins (CDs), cucurbiturils (CBs), calixarenes (CAs), and pillararenes (PAs) for various photocatalytic reactions. However, biomolecules and other supramolecular-host-related photocatalytic reactions are not included in this minireview. Generally, a
  • edge is hydrophobic, while the narrower lower edge is hydrophilic due to the presence of phenolic oxygen atoms. Depending on the number of phenol units, calixarenes have a variable cavity size, and thus are able to combine with different guests. Therefore, calixarenes can be used as effective
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Published 18 Jan 2021

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

  • Si-Yuan Liu,
  • Xin-Rui Wang,
  • Man-Ping Li,
  • Wen-Rong Xu and
  • Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

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  • C60 and C70 [1][2][3][4][5]. It is generally accepted that good complexation of fullerenes requires host molecules with bowl or basket-like shapes, such as calixarenes [6], corannulenes [7][8][9][10], cyclodextrins [11][12][13], cyclotriveratrylenes [14][15][16], and similar macrocycles [17][18][19
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Published 14 Oct 2020

NMR Spectroscopy of supramolecular chemistry on protein surfaces

  • Peter Bayer,
  • Anja Matena and
  • Christine Beuck

Beilstein J. Org. Chem. 2020, 16, 2505–2522, doi:10.3762/bjoc.16.203

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  • for improved selectivity and affinity. Examples for supramolecular ligands designed to recognize protein surfaces include tweezers [5][6][7][8][9][10][11][12][13][14][15][16][17][18], calixarenes [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38][39][40
  • supramolecular tweezers [5][6][7][8][9][10][11][12][13][14][15][16][17][18] as well as sulfonato- and phosphonato-calixarenes [19][20][21][22][23][24][25][26][27][28][29][30][31][32][33][34][35][36][37][38]. These ligands contain negatively charged functionalities interacting with the positively charged head
  • [8][9][10][11][12], and inhibit enzyme function [13] in vitro, they also exhibit interesting effects in vivo like the reversal of Alzheimer plaques in mice [14], tumor inhibition [15], and reduction of HIV infectivity [16], all while showing almost no toxic side effects [14][17]. In calixarenes with
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Published 09 Oct 2020

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

Graphical Abstract
  • compounds such as calixarenes, crown ethers and cyclodextrins, which can be used to form a stable inclusion complex with the drug, and improving the bioavailability of the drug [34][35]. Herein, we describe the results of the investigations of host–guest interactions between BALE and Q[8] in an aqueous
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Published 10 Jan 2020

Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

  • Sachin S. Burade,
  • Sushil V. Pawar,
  • Tanmoy Saha,
  • Navanath Kumbhar,
  • Amol S. Kotmale,
  • Manzoor Ahmad,
  • Pinaki Talukdar and
  • Dilip D. Dhavale

Beilstein J. Org. Chem. 2019, 15, 2419–2427, doi:10.3762/bjoc.15.234

Graphical Abstract
  • slides [46][47], steroids [48][49], calixpyrroles [50][51], calixarenes [52][53], and other scaffolds [54][55][56]. In particular, peptide based transmembrane anion transporters have attracted great interest. For example, Ghadiri [38], Ranganathan [39], and Granja [40] have independently reported
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Published 14 Oct 2019

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

Graphical Abstract
  • are also the epitome of complex-binding pockets of enzymes [3]. Macrocyclic arenes including calixarenes [4][5], resorcinarenes [6], cyclotriveratrylenes [7][8], pillararenes [9], biphen[n]arenes [10] and others [11][12] are all composed of hydroxy-substituted aromatic rings bridged by methylene or
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Published 26 Jul 2019

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

  • Piyali Sarkar,
  • Sayan Sarkar and
  • Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

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  • efficient organocatalysts due to their variable interacting sites. In this context, substituted calixarenes, cyclodextrins, etc., substances known for their ability to encapsulate organic guest molecules, have been explored as organocatalysts over the last two decades [19][20][21][22][23][24]. Another class
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Published 08 Jul 2019

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

Graphical Abstract
  • supramolecular cavities [25]. Calixarenes are the third generation of macrocyclic compounds composed of phenolic units bridged with methylene groups at the o-positions of phenolic hydroxy groups [9]. We have focused on molecular recognition and self-assembly of water-soluble calixarene derivatives for a long
  • time, directed by exploring biomedical applications of these compounds. Recently, we developed a series of guanidinium-modified calixarenes as novel artificial receptors [13][14]. We achieved ultrasensitive and specific fluorescence detection of lysophosphatidic acid (a cancer biomarker) by executing
  • behavior between GC5A and Fl [26]. The formation of a ground-state complex was confirmed by UV–vis titration, which revealed significant changes in band shapes and intensities. Upon fluorescence titration, the intrinsic emission of Fl was drastically quenched by gradual addition of GC5A. Given calixarenes
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Published 25 Jun 2019

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

Graphical Abstract
  • ; 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
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Published 18 Jun 2019

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

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  • 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
  • the well-studied cyclodextrins and crown ethers. Calixarenes are products of phenol–aldehyde condensation, as the aromatic components may derived from phenol, resorcinol, or pyrogallol; the aldehyde most often used for phenol is simple formaldehyde (methanal, HCHO), while larger aldehydes (e.g
  • calixarenes (with the same repeating units). The sulfur functionalities are stated to provide better metal complexation [3]. Unmodified calixarenes and thiacalixarenes are sparingly soluble, have chemical and thermal stability and act as host molecules as they possess cavities, but their inclusion properties
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Published 17 Jun 2019

Efficient synthesis of 4-substituted-ortho-phthalaldehyde analogues: toward the emergence of new building blocks

  • Clémence Moitessier,
  • Ahmad Rifai,
  • Pierre-Edouard Danjou,
  • Isabelle Mallard and
  • Francine Cazier-Dennin

Beilstein J. Org. Chem. 2019, 15, 721–726, doi:10.3762/bjoc.15.67

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  • deprotection agent was tested, trimethylsilyl iodide, as it was recently published by Danjou et al. [24] as a removal agent of methoxy groups on calixarenes architectures. Although we succeeded with the removal of methoxy groups, both aldehydes were reduced. Furthermore, the lithium chloride/N,N
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Published 19 Mar 2019

Polyaminoazide mixtures for the synthesis of pH-responsive calixarene nanosponges

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

Beilstein J. Org. Chem. 2019, 15, 633–641, doi:10.3762/bjoc.15.59

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  • . The desired responsivity to pH variations of the nanosponges obtained was verified by means of absorption tests on a set of organic pollutant model molecules. Keywords: calixarenes; nanosponges; pH-responsive materials; pollutants; polyaminoazides; Introduction The ability to provide a response to
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Published 12 Mar 2019

Ammonium-tagged ruthenium-based catalysts for olefin metathesis in aqueous media under ultrasound and microwave irradiation

  • Łukasz Gułajski,
  • Andrzej Tracz,
  • Katarzyna Urbaniak,
  • Stefan J. Czarnocki,
  • Michał Bieniek and
  • Tomasz K. Olszewski

Beilstein J. Org. Chem. 2019, 15, 160–166, doi:10.3762/bjoc.15.16

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  • in water including the development of specially designed water-soluble catalysts [21][22][23][24][25][26][27][28], addition of organic solvents [29][30][31], or use of additives such as for example calixarenes or cyclodextrins [32][33], chloride salts [34], vitamin E-based amphiphiles [35
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Published 17 Jan 2019

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

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  • USA 10.3762/bjoc.14.225 Abstract Some of the least studied calixarenes are those that consist of azulene rings bridged by -CH2- groups. Since Lash and Colby’s discovery of a simple and convenient method for producing the parent all-hydrocarbon calix[4]azulene, there have been two other all
  • 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
  • just a few. Reinhoudt has recently presented an overview of the historical evolution of the chemistry of the calixarenes [1]. Supramolecular applications, in particular, of many of the great number of creative derivatives of calixarenes which have been and continue to be synthesized are widely being
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Published 25 Sep 2018

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

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  • , 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
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Published 27 Aug 2018

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

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  • -flat wheels, such as calixarenes or cyclodextrins, are threaded along an axle to give a pseudo[3]rotaxane architecture V–VII (Figure 2), where three sequential stereoisomers can arise. We showed that this stereoisomerism can be effectively controlled when two calix[6]arene wheels are threaded along a
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Published 14 Aug 2018

Synthesis of new p-tert-butylcalix[4]arene-based polyammonium triazolyl amphiphiles and their binding with nucleoside phosphates

  • Vladimir A. Burilov,
  • Guzaliya A. Fatikhova,
  • Mariya N. Dokuchaeva,
  • Ramil I. Nugmanov,
  • Diana A. Mironova,
  • Pavel V. Dorovatovskii,
  • Victor N. Khrustalev,
  • Svetlana E. Solovieva and
  • Igor S. Antipin

Beilstein J. Org. Chem. 2018, 14, 1980–1993, doi:10.3762/bjoc.14.173

Graphical Abstract
  • ]. Calixarenes are easily functionalized at both their upper and lower rims with various stereoisomers obtainable; the initial macrocycles can be synthesized in a simple manner, they are not toxic, etc. [17][18][19][20][21][22]. Amphiphilic calixarenes are particularly interesting because they can be regarded as
  • established by 1H and 13C NMR spectroscopy as well as by IR spectroscopy and MALDI–TOF mass spectrometry. Their compositions were determined by elementary analysis. A standard set of signals typical for distal disubstituted calixarenes was found in the 1H NMR spectra of 4a and b (Supporting Information File 1
  • are assigned to the different natures of the used dyes. In the case of EY, which is a dianion at pH 7, the interaction with the dicationic calixarenes 10a,b results in the formation of a non-charged complex, which can be referred to a non-ionic surfactant. Generally, non-ionic surfactants possess
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Published 31 Jul 2018

Asymmetric Michael addition reactions catalyzed by calix[4]thiourea cyclohexanediamine derivatives

  • Zheng-Yi Li,
  • Hong-Xiao Tong,
  • Yuan Chen,
  • Hong-Kui Su,
  • Tangxin Xiao,
  • Xiao-Qiang Sun and
  • Leyong Wang

Beilstein J. Org. Chem. 2018, 14, 1901–1907, doi:10.3762/bjoc.14.164

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  • and yields of the Michael reactions. Supramolecular catalysis has drawn tremendous interest in the past few years [15][16][17][18][19][20][21][22][23]. In this context, calixarenes are ideal supramolecular macrocyclic scaffolds for the design of molecular receptors and organocatalysts due to their
  • , this may offer us the opportunity to improve the green aspect of many reactions both in organic and aqueous medium [30]. For example, it has been reported that calixarenes linked with thiourea groups can be used to catalyze asymmetric Aldol reactions or Michael addition reactions in recent years [31
  • ][32][33]. Compared with the lower rim in the cone conformation of calixarenes, the functionalization of the upper rim is more challenging. Notably, it should be more valuable to exploit the cavity of upper rim-functionalized calixarenes because of the possibility of simultaneously using the
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Published 25 Jul 2018

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

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  • particularly suitable for the detection of analytes lacking chromophores. The key factor in IDA is the rational design of artificial receptors that are capable of binding analytes strongly and specifically. Calixarenes are the third generation of macrocyclic receptors after crown ethers and cyclodextrins. Due
  • to their facial modification, Prof. Böhmer demonstrated calixarenes as having “(almost) unlimited possibilities” [17]. We have focused on molecular recognition and self-assembly of water-soluble calixarene derivatives for a long time [18][19][20][21][22][23][24], directed by exploring biomedical
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Published 19 Jul 2018

Synthesis and photophysical studies of a multivalent photoreactive RuII-calix[4]arene complex bearing RGD-containing cyclopentapeptides

  • Sofia Kajouj,
  • Lionel Marcelis,
  • Alice Mattiuzzi,
  • Adrien Grassin,
  • Damien Dufour,
  • Pierre Van Antwerpen,
  • Didier Boturyn,
  • Eric Defrancq,
  • Mathieu Surin,
  • Julien De Winter,
  • Pascal Gerbaux,
  • Ivan Jabin and
  • Cécile Moucheron

Beilstein J. Org. Chem. 2018, 14, 1758–1768, doi:10.3762/bjoc.14.150

Graphical Abstract
  • involved in the angiogenesis process [60]. Furthermore, the use of calixarenes for biological applications is the subject of intensive researches. They are indeed exploited in various areas such as surface recognition, structural mimes or membrane receptor inhibition [61][62][63], and it was also shown
  • that calixarenes themselves display antibacterial, antiviral, and anticancer properties [64]. Herein, we describe the synthesis of a multivalent phototherapeutic agent designed in order to specifically target membrane receptors involved in the angiogenesis process. The multivalent system is composed of
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Published 16 Jul 2018

Host–guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides: solid-state, solution and computational studies

  • Rakesh Puttreddy,
  • Ngong Kodiah Beyeh,
  • S. Maryamdokht Taimoory,
  • Daniel Meister,
  • John F. Trant and
  • Kari Rissanen

Beilstein J. Org. Chem. 2018, 14, 1723–1733, doi:10.3762/bjoc.14.146

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  • intramolecular O···H–O hydrogen bonds (HBs) [1][2]. The combination of their confined cavity and conformational flexibility has driven the interest in these synthetic receptors [3], a subclass of calixarenes [4], for a wide range of applications in fields such as catalysis [5][6][7][8][9], sensors [10][11
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Published 10 Jul 2018
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