Colorimetric anion sensing by polyamide models containing urea-binding sites

Novel colorimetric polyamide model compounds for anion-sensing applications are described. Light beige solutions of one of the models (M3) in DMSO develop a red to yellow-reddish colour upon addition of some anions, including OH− , F− , HC , P , AcO− , benzoate− , oxalate2 − and p-toluenesulphonate− . In contrast, they remain unchanged in the presence of CH2ClC , H2P , CF3CO2 − , Br− , methanesulphonate− , Cl− or I− . The reddish colour caused by the addition of basic anions is due to the deprotonation of the urea groups, while the yellowish colour corresponds to the modification of the electron density surrounding the urea group due to complexation. The development of the yellow colour of DMSO solutions of M3 upon addition of acetate ions and the disappearance of the red colour of solutions of M3/fluoride by the displacement of acetate ions can serve as a novel colorimetric assay for the titration of the acetate anion, with detection limits close to 1 ppb. The host:guest stoichiometry (polyamide model compound:anion complexes) and the stability constants of complexes were determined by 1H NMR.

[1]  Philip A. Gale,et al.  Anion Receptor Chemistry , 2016 .

[2]  J. García,et al.  Recent Patents on Aromatic Polyamides , 2009 .

[3]  V. Calderón,et al.  Polyamide model compound containing the urea group as selective colorimetric sensing probe towards aromatic diamines , 2009 .

[4]  V. Calderón,et al.  The extraction of environmentally polluting cations from aqueous media with novel polyamides containing cation‐ and anion‐selective host units , 2009 .

[5]  F. García,et al.  Fluorescent aromatic polyamides with urea binding sites and fluorene or dansyl signaling units , 2008 .

[6]  V. Calderón,et al.  Novel aliphatic–aromatic poly(amide urea)s: Synthesis, characterization and application to the elimination of environmentally toxic heavy metal ions , 2008 .

[7]  V. Calderón,et al.  Selective solid–liquid extraction of cations using solid-phase polyamides with crown ether moieties as cation host units , 2007 .

[8]  T. Muster,et al.  A Review of Surface Functionalized Amine Terminated Dendrimers for Application in Biological and Molecular Sensing , 2007 .

[9]  A. Valente,et al.  Crown moieties as cation host units in model polyamide compounds: Application in liquid–liquid cation extraction and in membrane cation transport , 2007 .

[10]  R. Martínez‐Máñez,et al.  Chromogenic signaling of hydrogen carbonate anion with pyrylium-containing polymers. , 2007, Organic letters.

[11]  A. Pais,et al.  Aqueous solution and solid state interactions of lanthanide ions with a methacrylic ester polymer bearing pendant 15‐crown‐5 moieties , 2007 .

[12]  Aurelia Pastor,et al.  Structure, stability and guest affinity of tris(3-ureidobenzyl)amine capsules in solution. , 2007, Chemistry.

[13]  D. H. Burns.  Anion Receptor Chemistry , 2006 .

[14]  P. Molina,et al.  Ferrocene-based ureas as multisignaling receptors for anions. , 2006, The Journal of organic chemistry.

[15]  Philip A. Gale,et al.  Neutral Pyrrole Systems , 2006 .

[16]  Carmen Peinado,et al.  Fluorescent probes for sensing processes in polymers. , 2005, Chemistry.

[17]  M. Licchelli,et al.  Why, on interaction of urea-based receptors with fluoride, beautiful colors develop. , 2005, The Journal of organic chemistry.

[18]  R. Martínez‐Máñez,et al.  New Advances in Fluorogenic Anion Chemosensors , 2005, Journal of Fluorescence.

[19]  M. Márquez,et al.  Materials chemistry approach to anion-sensor design , 2004 .

[20]  A. Ojida,et al.  Molecular recognition in a supramolecular hydrogel to afford a semi-wet sensor chip. , 2004, Journal of the American Chemical Society.

[21]  P. Anzenbacher,et al.  Sensing of aqueous phosphates by polymers with dual modes of signal transduction. , 2004, Journal of the American Chemical Society.

[22]  J. Steed,et al.  Self-assembly of tris(2-ureidobenzyl)amines: a new type of capped, capsule-like dimeric aggregates derived from a highly flexible skeleton. , 2004, Chemistry.

[23]  José M. García,et al.  Lanthanide Ion Interaction with a Crown Ether Methacrylic Polymer, Poly(1,4,7,10-tetraoxacyclododecan-2-ylmethyl methacrylate), as Seen by Spectroscopic, Calorimetric, and Theoretical Studies , 2004 .

[24]  Félix Sancenón,et al.  Fluorogenic and chromogenic chemosensors and reagents for anions. , 2003, Chemical reviews.

[25]  A. Ojida,et al.  Cross-linking strategy for molecular recognition and fluorescent sensing of a multi-phosphorylated peptide in aqueous solution. , 2003, Journal of the American Chemical Society.

[26]  W. Al-Soufi,et al.  Determination of second-order association constants by global analysis of 1 H and 13 C NMR chemical shifts. Application to the complexation of sodium fusidate and potassium helvolate by β- and γ-cyclodextrin , 2003, Steroids.

[27]  E. Álvarez-Parrilla,et al.  Complexation of Bile Salts by Natural Cyclodextrins , 2003 .

[28]  J. Steed,et al.  Dimeric self-assembling capsules derived from the highly flexible tribenzylamine skeleton. , 2002, The Journal of organic chemistry.

[29]  Itaru Hamachi,et al.  First thermally responsive supramolecular polymer based on glycosylated amino acid. , 2002, Journal of the American Chemical Society.

[30]  R. Martínez‐Máñez,et al.  Selective fluoride sensing using colorimetric reagents containing anthraquinone and urea or thiourea binding sites , 2002 .

[31]  H. Schneider,et al.  Complexation of Anions Including Nucleotide Anions by Open-Chain Host Compounds with Amide, Urea, and Aryl Functions , 2000 .

[32]  D. Reinhoudt,et al.  Thio)urea resorcinarene cavitands. Complexation and membrane transport of halide anions , 1998 .

[33]  K. A. Connors,et al.  Binding Constants: The Measurement of Molecular Complex Stability , 1987 .

[34]  A. S. Solovkin,et al.  THE CHEMISTRY OF AQUEOUS SOLUTIONS OF ZIRCONIUM SALTS (DOES THE ZIRCONYL ION EXIST , 1962 .

[35]  D. F. Kutepov.  CHEMICAL ADVANCES IN SYNTHESIS AND REACTIONS OF DIARYLUREAS , 1962 .