Synthesis of a cationic water-soluble pillar[6]arene and its effective complexation towards naphthalenesulfonate guests.

A novel positively charged pillar[6]arene derivative bearing twelve pyridinium moieties has been synthesized. Its efficient complexation behavior towards two anionic naphthalenesulfonate substrates in aqueous media is described.

[1]  Yoshiaki Nakamoto,et al.  para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property. , 2008, Journal of the American Chemical Society.

[2]  D. Fitzmaurice,et al.  Introducing negative charges into bis-p-phenylene crown ethers: a study of bipyridinium-based [2]pseudorotaxanes and [2]rotaxanes. , 2008, Chemistry.

[3]  Jiuming He,et al.  A cationic water-soluble pillar[5]arene: synthesis and host-guest complexation with sodium 1-octanesulfonate. , 2011, Chemical communications.

[4]  Yu Liu,et al.  A Comparative Study of Complexation of β-Cyclodextrin, Calix[4]arenesulfonate and Cucurbit[7]uril with Dye Guests: Fluorescence Behavior and Binding Ability , 2007 .

[5]  H. Pal,et al.  Cucurbit[n]uril based supramolecular assemblies: tunable physico-chemical properties and their prospects. , 2011, Chemical communications.

[6]  He Tian,et al.  Recent progress on switchable rotaxanes. , 2006, Chemical Society reviews.

[7]  J. F. Stoddart,et al.  Monofunctionalized pillar[5]arene as a host for alkanediamines. , 2011, Journal of the American Chemical Society.

[8]  J. Nierengarten,et al.  The high yielding synthesis of pillar[5]arenes under Friedel-Crafts conditions explained by dynamic covalent bond formation. , 2012, Chemical communications.

[9]  Ming Jiang,et al.  Cyclodextrin-based inclusion complexation bridging supramolecular chemistry and macromolecular self-assembly. , 2011, Chemical Society reviews.

[10]  Y. Yu,et al.  Supramolecular Polymers Based on Efficient Pillar[5]arene-Neutral Guest Motifs. , 2013, Chemistry.

[11]  Jiuming He,et al.  A new water-soluble pillar[5]arene: synthesis and application in the preparation of gold nanoparticles. , 2012, Chemical communications.

[12]  T. Ogoshi,et al.  Synthesis of novel pillar-shaped cavitands “Pillar[5]arenes” and their application for supramolecular materials , 2012, Journal of Inclusion Phenomena and Macrocyclic Chemistry.

[13]  Lingyun Wang,et al.  A facile and efficient preparation of pillararenes and a pillarquinone. , 2009, Angewandte Chemie.

[14]  Yu Liu,et al.  Highly effective binding of viologens by p-sulfonatocalixarenes for the treatment of viologen poisoning. , 2009, Journal of medicinal chemistry.

[15]  Xiao‐Yu Hu,et al.  Novel pillar[5]arene-based dynamic polyrotaxanes interlocked by the quadruple hydrogen bonding ureidopyrimidinone motif. , 2012, Organic letters.

[16]  L. Isaacs Cucurbit[n]urils: from mechanism to structure and function. , 2009, Chemical communications.

[17]  Y. Yu,et al.  Self-assembly of [2]pseudorotaxanes based on pillar[5]arene and bis(imidazolium) cations. , 2010, Chemical communications.

[18]  Lyle Isaacs,et al.  Acyclic cucurbit[n]uril molecular containers enhance the solubility and bioactivity of poorly soluble pharmaceuticals , 2012, Nature Chemistry.

[19]  S. Shinkai,et al.  NMR and crystallographic studies of a p-sulfonatocalix(4)arene-guest complex , 1990 .

[20]  T. Ogoshi,et al.  Synthesis, conformational and host-guest properties of water-soluble pillar[5]arene. , 2010, Chemical communications.

[21]  Zhan-Ting Li,et al.  Pillar[n]arenes (n = 8-10) with two cavities: synthesis, structures and complexing properties. , 2012, Chemical communications.

[22]  F. Perret,et al.  Biochemistry of the para-sulfonato-calix[n]arenes. , 2006, Chemical communications.

[23]  Jun-Li Hou,et al.  Single-molecular artificial transmembrane water channels. , 2012, Journal of the American Chemical Society.

[24]  Yu Liu,et al.  The structure and thermodynamics of calix[n]arene complexes with dipyridines and phenanthroline in aqueous solution studied by microcalorimetry and NMR spectroscopy. , 2006, The journal of physical chemistry. B.

[25]  Feihe Huang,et al.  A solvent-driven molecular spring , 2012 .

[26]  K. Sharma,et al.  Pillar[5]arenes: fascinating cyclophanes with a bright future. , 2012, Chemical Society reviews.

[27]  Chunju Li,et al.  Complexation of neutral 1,4-dihalobutanes with simple pillar[5]arenes that is dominated by dispersion forces. , 2012, Organic & biomolecular chemistry.

[28]  Artur Makarewicz,et al.  Electronic Supplementary Material ( ESI ) for ChemComm , 2015 .

[29]  Zhenxia Chen,et al.  Synthesis of pillar[5]arene dimers and their cooperative binding toward some neutral guests. , 2012, Organic letters.

[30]  S. J. Loeb,et al.  Cooperative ion-ion interactions in the formation of interpenetrated molecules. , 2008, Angewandte Chemie.

[31]  Juyoung Yoon,et al.  Chemosensors for pyrophosphate. , 2009, Accounts of chemical research.

[32]  Leyong Wang,et al.  Pillar[5]arene-based polymeric architectures constructed by orthogonal supramolecular interactions. , 2012, Chemical communications.

[33]  Wen Si,et al.  Selective artificial transmembrane channels for protons by formation of water wires. , 2011, Angewandte Chemie.

[34]  Yanli Zhao,et al.  Host-guest complexation driven dynamic supramolecular self-assembly. , 2013, Organic & biomolecular chemistry.

[35]  Y. Yu,et al.  Complexation of 1,4-bis(pyridinium)butanes by negatively charged carboxylatopillar[5]arene. , 2011, The Journal of organic chemistry.

[36]  H. Pal,et al.  Photophysical Properties and Rotational Relaxation Dynamics of Neutral Red Bound to β-Cyclodextrin , 2004 .

[37]  P. Workman,et al.  Molecular biology: Choose your protein partners , 2012, Nature.

[38]  Jae Wook Lee,et al.  Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. , 2003, Accounts of chemical research.

[39]  Lyle Isaacs,et al.  The cucurbit[n]uril family. , 2005, Angewandte Chemie.

[40]  Ying-Wei Yang,et al.  Viologen-mediated assembly of and sensing with carboxylatopillar[5]arene-modified gold nanoparticles. , 2013, Journal of the American Chemical Society.

[41]  Feihe Huang,et al.  Preparation of Pillar[n]arenes by Cyclooligomerization of 2,5‐Dialkoxybenzyl Alcohols or 2,5‐Dialkoxybenzyl Bromides , 2011 .

[42]  B. Iverson,et al.  Synthesis and Conformational Characterization of Tethered, Self-Complexing 1,5-Dialkoxynaphthalene/1,4,5,8-Naphthalenetetracarboxylic Diimide Systems , 2000 .

[43]  Yong Yang,et al.  Pillararenes, a new class of macrocycles for supramolecular chemistry. , 2012, Accounts of chemical research.

[44]  Feihe Huang,et al.  Syntheses of copillar[5]arenes by co-oligomerization of different monomers. , 2010, Organic letters.

[45]  Yu Liu,et al.  Operational calixarene-based fluorescent sensing systems for choline and acetylcholine and their application to enzymatic reactions , 2011 .

[46]  Zhenxia Chen,et al.  Highly effective binding of neutral dinitriles by simple pillar[5]arenes. , 2012, Chemical communications.

[47]  Young Ho Ko,et al.  Functionalized cucurbiturils and their applications. , 2007, Chemical Society reviews.

[48]  Antoine Taly,et al.  Ligand-gated ion channels: new insights into neurological disorders and ligand recognition. , 2012, Chemical reviews.

[49]  J. F. Stoddart,et al.  Dynamic clicked surfaces based on functionalised pillar[5]arene. , 2011, Chemical communications.

[50]  Ying-Wei Yang,et al.  One-pot synthesis of pillar[n]arenes catalyzed by a minimum amount of TfOH and a solution-phase mechanistic study. , 2012, Organic & biomolecular chemistry.

[51]  Feihe Huang,et al.  A water-soluble pillar[6]arene: synthesis, host-guest chemistry, and its application in dispersion of multiwalled carbon nanotubes in water. , 2012, Journal of the American Chemical Society.

[52]  T. Boiński,et al.  A facile, moisture-insensitive method for synthesis of pillar[5]arenes—the solvent templation by halogen bonds , 2012 .

[53]  Yanli Zhao,et al.  Thermo-responsive fluorescent vesicles assembled by fluorescein-functionalized pillar[5]arene , 2013 .

[54]  L. Barbour,et al.  Controlling molecular self-organization: formation of nanometer-scale spheres and tubules , 1999, Science.

[55]  Chunju Li,et al.  Pillar[5]arene–neutral guest recognition based supramolecular alternating copolymer containing [c2]daisy chain and bis-pillar[5]arene units , 2013 .

[56]  E. Dalcanale,et al.  Supramolecular sensing with phosphonate cavitands. , 2013, Accounts of chemical research.

[57]  H. Zhang,et al.  High affinity crown ether complexes in water: thermodynamic analysis, evidence of crystallography and binding of NAD+. , 2012, The Journal of organic chemistry.

[58]  Y. Yu,et al.  Molecular selective binding of basic amino acids by a water-soluble pillar[5]arene. , 2013, Chemical communications.

[59]  J. Fraser Stoddart,et al.  Cyclodextrin-Based Catenanes and Rotaxanes. , 1998, Chemical reviews.

[60]  Chunju Li,et al.  Complex interactions of pillar[5]arene with paraquats and bis(pyridinium) derivatives. , 2010, Organic & biomolecular chemistry.

[61]  W. Nau Supramolecular capsules: under control. , 2010, Nature chemistry.

[62]  Yong Chen,et al.  Cyclodextrin-based bioactive supramolecular assemblies. , 2010, Chemical Society reviews.

[63]  Feihe Huang,et al.  pH-responsive supramolecular polymerization in aqueous media driven by electrostatic attraction-enhanced crown ether-based molecular recognition. , 2012, Macromolecular rapid communications.

[64]  Y. Yu,et al.  Novel neutral guest recognition and interpenetrated complex formation from pillar[5]arenes. , 2011, Chemical communications.

[65]  Zhi Ma,et al.  Formation of linear supramolecular polymers that is driven by C-H⋅⋅⋅π interactions in solution and in the solid state. , 2011, Angewandte Chemie.

[66]  Yu Liu,et al.  Calixarene-based supramolecular polymerization in solution. , 2012, Chemical Society reviews.