Amide-functionalized pillar[5]arenes as a novel class of macrocyclic receptors for the sensing of H2PO4- anion.

A novel class of amide-functionalized pillar[5]arenes, that is, alkyl and aryl amide derivatives, has been synthesized. Highly selective binding of the dihydrogen phosphate anion over a range of anions by the new synthetic receptors is reported. First, the "binding strength-selectivity" relationship has been decided for the pillar[5]arene/anion systems.

[1]  L. Yakimova,et al.  Synthesis of p-tert-butylthiacalix[4]arenes functionalized with tris(2-aminoethyl)amine fragments at the lower rim and their interaction with model lipid membranes , 2014 .

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

[3]  D. Shurpik,et al.  Highly selective binding of methyl orange dye by cationic water-soluble pillar[5]arenes. , 2016, Organic & biomolecular chemistry.

[4]  G. Evtugyn,et al.  ELECTROCHEMICAL BEHAVIOR OF PILLAR[5]ARENE ON GLASSY CARBON ELECTRODE AND ITS INTERACTION WITH Cu2+ AND Ag+ IONS , 2014 .

[5]  V. Lippolis,et al.  Tailoring cyclic polyamines for inorganic/organic phosphate binding. , 2010, Chemical Society reviews.

[6]  P. Dydio,et al.  A hybrid macrocyclic anion receptor exploiting the pyrrole-2,5-diacetamide unit , 2016 .

[7]  Chuan-feng Chen,et al.  A Highly Selective Fluorescent Chemosensor for H2PO4– Based on a Calix[4]arene Tetraamide Derivative , 2005 .

[8]  Maurizio Licchelli,et al.  Urea vs. thiourea in anion recognition. , 2005, Organic & biomolecular chemistry.

[9]  Philip A. Gale.  Amidopyrroles: from anion receptors to membrane transport agents. , 2005, Chemical communications.

[10]  B. Hay.  De novo structure-based design of anion receptors. , 2010, Chemical Society reviews.

[11]  Luigi Fabbrizzi,et al.  Anion recognition by hydrogen bonding: urea-based receptors. , 2010, Chemical Society reviews.

[12]  H. Meier,et al.  Pillar[n]arenes—a Novel, Highly Promising Class of Macrocyclic Host Molecules , 2014 .

[13]  Philip A. Gale,et al.  Preface: supramolecular chemistry of anionic species themed issue , 2010 .

[14]  Feihe Huang,et al.  Photo-responsive self-assembly based on a water-soluble pillar[6]arene and an azobenzene-containing amphiphile in water. , 2014, Chemical communications.

[15]  E. Monzani,et al.  Chiral receptors for phosphate ions. , 2005, Organic & biomolecular chemistry.

[16]  Feihe Huang,et al.  A non-symmetric pillar[5]arene-based selective anion receptor for fluoride. , 2012, Chemical communications.

[17]  G. Zaragoza,et al.  A chemosensor for dihydrogenphosphate based on an oxoazamacrocycle possessing three thiourea arms. , 2012, Organic & biomolecular chemistry.

[18]  I. Stoikov,et al.  Phosphorus-bridged calixarene phosphites: dramatic influence of a tert-butyl group at the upper rim of the macrocycle upon anion binding , 2010 .

[19]  Philip A. Gale,et al.  Anion Recognition in Supramolecular Chemistry , 2010 .

[20]  Thawatchai Tuntulani,et al.  Chromogenic anion sensors. , 2003, Chemical Society reviews.

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

[22]  Feihe Huang,et al.  Water-soluble pillar[7]arene: synthesis, pH-controlled complexation with paraquat, and application in constructing supramolecular vesicles. , 2014, Organic letters.

[23]  Jong‐In Hong,et al.  A fluorescent pyrophosphate sensor via excimer formation in water. , 2005, Chemical communications.

[24]  J. Sessler,et al.  Neutral CH and cationic CH donor groups as anion receptors. , 2014, Chemical Society reviews.

[25]  J. Sessler,et al.  Artificial receptors for the recognition of phosphorylated molecules. , 2011, Chemical reviews.

[26]  L. Yakimova,et al.  Synthesis of Photo-Switchable Derivatives of p-tert-Butyl Thiacalix(4)arenes Containing Ethoxycarbonyl and 4-Amidoazobenzene Fragments in the Lower Rim Substituents , 2013 .

[27]  L. Yakimova,et al.  Pillar(5)arenes with Morpholide and Pyrrolidide Substituents: Synthesis and Complex Formation with Alkali Metal Ions , 2014 .

[28]  P. Zheng,et al.  Thermodynamics and coordination characteristics of the hydronium-uranium(VI)-dicyclohexano-24-crown-8 extraction complex , 1988 .

[29]  Claudia Caltagirone,et al.  Applications of Supramolecular Anion Recognition. , 2015, Chemical reviews.

[30]  L. Yakimova,et al.  Synthesis of hybrid nano- and microsized particles on the base of colloid silica and thiacalix[4]arene derivatives , 2013, Journal of Nanoparticle Research.

[31]  Philip A. Gale,et al.  From anion receptors to transporters. , 2011, Accounts of chemical research.

[32]  Yoshiaki Nakamoto,et al.  Pillar-Shaped Macrocyclic Hosts Pillar[n]arenes: New Key Players for Supramolecular Chemistry. , 2016, Chemical reviews.

[33]  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.

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

[35]  S. Adeloju,et al.  Progress and recent advances in phosphate sensors: a review. , 2013, Talanta.

[36]  Jianzhuang Chen,et al.  An amphiphilic pillar[5]arene: synthesis, controllable self-assembly in water, and application in calcein release and TNT adsorption. , 2012, Journal of the American Chemical Society.

[37]  T. Gunnlaugsson,et al.  Colorimetric sensing of anions in aqueous solution using a charge neutral, cleft-like, amidothiourea receptor: tilting the balance between hydrogen bonding and deprotonation in anion recognition. , 2008, Organic & biomolecular chemistry.

[38]  I. Stoikov,et al.  Synthetic receptors based on calix[4]arene functionalized at the lower rim in molecular recognition of dicarboxylic, α-hydroxycarboxylic, and α-amino acids , 2004 .

[39]  L. Yakimova,et al.  MALDI-TOF MS and Morphology Studies of Thiacalixarene-Silsesquioxane Products of Oligo- and Polycondensation , 2014, Silicon.

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

[41]  Pierre Kennepohl,et al.  Evidence for Halogen Bond Covalency in Acyclic and Interlocked Halogen-Bonding Receptor Anion Recognition , 2014, Journal of the American Chemical Society.

[42]  T. Ogoshi,et al.  Planar-chiral macrocyclic host pillar[5]arene: no rotation of units and isolation of enantiomers by introducing bulky substituents. , 2011, Organic letters.

[43]  Broder,et al.  Phosphorylation of 3'-azido-3'-deoxythymidine and selective interaction of the 5'-triphosphate with human immunodeficiency virus reverse transcriptase. , 1986, Proceedings of the National Academy of Sciences of the United States of America.

[44]  Philip A. Gale.  Anion receptor chemistry: highlights from 2008 and 2009. , 2010, Chemical Society reviews.

[45]  Wolfram Saenger,et al.  Principles of Nucleic Acid Structure , 1983 .

[46]  Thorfinnur Gunnlaugsson,et al.  Colorimetric and fluorescent anion sensors: an overview of recent developments in the use of 1,8-naphthalimide-based chemosensors. , 2010, Chemical Society reviews.

[47]  S. Kondo,et al.  Selective detection of dihydrogen phosphate anion by fluorescence change with tetraamide-based receptors bearing isoquinolyl and quinolyl moieties. , 2013, Organic letters.

[48]  L. Yakimova,et al.  Selective stepwise oxidation of 1,4-decamethoxypillar[5]arene , 2015 .

[49]  A. Soares,et al.  Sensing and analysis of soluble phosphates in environmental samples: a review. , 2013, Biosensors & bioelectronics.

[50]  K. Ghosh,et al.  Pyridinium amide-based simple synthetic receptor for selective recognition of dihydrogenphosphate , 2009 .

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

[52]  Xiaofan Ji,et al.  A dual-responsive supra-amphiphilic polypseudorotaxane constructed from a water-soluble pillar[7]arene and an azobenzene-containing random copolymer. , 2015, Journal of the American Chemical Society.

[53]  J. Cochrane,et al.  Recent advances in H2PO4− fluorescent sensors , 2014 .

[54]  Itaru Hamachi,et al.  Molecular recognition and fluorescence sensing of monophosphorylated peptides in aqueous solution by bis(zinc(II)-dipicolylamine)-based artificial receptors. , 2004, Journal of the American Chemical Society.