Fluoride binding in water with the use of micellar nanodevices based on salophen complexes.

The use of micelles to transpose lipophilic receptors, such as uranyl-salophen complexes, into an aqueous environment is a valuable and versatile tool. Receptor 1 incorporated into CTABr micelles forms a supramolecular system that exhibits excellent binding properties towards fluoride in water, despite the competition of the aqueous medium. To fully evaluate the potential of micellar nanodevices, we extended our previous study to other types of surfactants and to a uranyl-salophen receptor with a more extended aromatic surface. Paramagnetic relaxation enhancement experiments were used to obtain information on the location of the two receptors within the micelles and complementary information was obtained from dynamic light scattering experiments. With these data it is possible to account for the key factors necessary to obtain an efficient supramolecular device for anion binding in water.

[1]  S. Bhattacharya,et al.  An efficient probe for rapid detection of cyanide in water at parts per billion levels and naked-eye detection of endogenous cyanide. , 2014, Chemistry, an Asian journal.

[2]  R. Martínez‐Máñez,et al.  A surfactant-assisted probe for the chromo-fluorogenic selective recognition of GSH in water. , 2014, Organic & biomolecular chemistry.

[3]  A. Dorazco‐González.  Chemosensing of Chloride Based on a Luminescent Platinum(II) NCN Pincer Complex in Aqueous Media , 2014 .

[4]  K. Bartik,et al.  Paramagnetic relaxation enhancement experiments: a valuable tool for the characterization of micellar nanodevices. , 2013, The journal of physical chemistry. B.

[5]  N. Dey,et al.  Selective and efficient detection of nitro-aromatic explosives in multiple media including water, micelles, organogel, and solid support. , 2013, ACS applied materials & interfaces.

[6]  C. de Castro,et al.  A route to oligosaccharide-appended salicylaldehydes: useful building blocks for the synthesis of metal-salophen complexes. , 2013, The Journal of organic chemistry.

[7]  K. Rissanen,et al.  A zinc-salophen/bile-acid conjugate receptor solubilized by CTABr micelles binds phosphate in water. , 2013, Organic & biomolecular chemistry.

[8]  R. Martínez‐Máñez,et al.  An Instantaneous and Highly Selective Chromofluorogenic Chemodosimeter for Fluoride Anion Detection in Pure Water , 2013, ChemistryOpen.

[9]  N. Dey,et al.  Ratiometric, reversible, and parts per billion level detection of multiple toxic transition metal ions using a single probe in micellar media. , 2013, ACS applied materials & interfaces.

[10]  K. Rissanen,et al.  Highlights on contemporary recognition and sensing of fluoride anion in solution and in the solid state. , 2013, Chemical Society reviews.

[11]  K. Bartik,et al.  Monitoring Fluoride Binding in DMSO: Why is a Singular Binding Behavior Observed? , 2012 .

[12]  K. Zangger,et al.  Probing the interactions of macrolide antibiotics with membrane-mimetics by NMR spectroscopy. , 2012, Journal of medicinal chemistry.

[13]  J. Rebek,et al.  Activation of a water-soluble resorcinarene cavitand at the water-phosphocholine micelle interface. , 2011, Journal of the American Chemical Society.

[14]  S. Bhattacharya,et al.  Colorimetric probes based on anthraimidazolediones for selective sensing of fluoride and cyanide ion via intramolecular charge transfer. , 2011, The Journal of organic chemistry.

[15]  A. Dalla Cort,et al.  Anion recognition in water with use of a neutral uranyl-salophen receptor. , 2011, The Journal of organic chemistry.

[16]  Lorenzo Mosca,et al.  Urea-, squaramide-, and sulfonamide-based anion receptors: a thermodynamic study. , 2011, Chemistry.

[17]  Davy Sinnaeve,et al.  NMR study of the influence of pH on phenol sorption in cationic CTAB micellar solutions , 2010 .

[18]  K. Schenk,et al.  Turn-off-and-on: chemosensing ensembles for sensing chloride in water by fluorescence spectroscopy. , 2010, Inorganic chemistry.

[19]  A. Dalla Cort,et al.  Metal-salophen-based receptors for anions. , 2010, Chemical Society reviews.

[20]  K. Severin,et al.  A micelle-based chemosensing ensemble for the fluorimetric detection of chloride in water. , 2010, Chemistry.

[21]  C. Wade,et al.  Fluoride ion complexation and sensing using organoboron compounds. , 2010, Chemical reviews.

[22]  D. Otzen,et al.  Quantitative Use of Paramagnetic Relaxation Enhancements for Determining Orientations and Insertion Depths of Peptides in Micelles , 2009, Chembiochem : a European journal of chemical biology.

[23]  D. Hertel,et al.  Fluoride recognition by a chiral urea receptor linked to a phthalimide chromophore. , 2009, Organic & biomolecular chemistry.

[24]  K. Rissanen,et al.  Recognition and sensing of fluoride anion. , 2009, Chemical communications.

[25]  K. Zangger,et al.  Positioning of micelle-bound peptides by paramagnetic relaxation enhancements. , 2009, The journal of physical chemistry. B.

[26]  K. Bartik,et al.  Fluoride binding in water: a new environment for a known receptor. , 2008, Chemphyschem : a European journal of chemical physics and physical chemistry.

[27]  K. Rissanen,et al.  Specific recognition of fluoride anion using a metallamacrocycle incorporating a uranyl-salen unit , 2008 .

[28]  V. Aswal,et al.  Structural Changes in Micelles of Different Sizes on Hydrocarbon Solubilization as Studied by SANS , 2008 .

[29]  O. Reinaud,et al.  Self-assembly via ionic interactions of calix[6]arene-based receptors displaying remarkable host–guest properties toward neutral guests , 2007 .

[30]  J. Rebek,et al.  Guest recognition with micelle-bound cavitands. , 2007, Journal of the American Chemical Society.

[31]  K. Rissanen,et al.  Recognition of alkali metal halide contact ion pairs by uranyl-salophen receptors bearing aromatic sidearms. The role of cation-pi interactions. , 2005, Journal of the American Chemical Society.

[32]  E. Monzani,et al.  Nature of urea-fluoride interaction: incipient and definitive proton transfer. , 2004, Journal of the American Chemical Society.

[33]  S. Giampaolo,et al.  Study of Intermicellar Interactions and Micellar Sizes in Ionic Micelle Solutions by Comparing Collective Diffusion and Self-Diffusion Coefficients , 2004 .

[34]  K. Rissanen,et al.  Uranyl-salophen based ditopic receptors for the recognition of quaternary ammonium halides. , 2003, Chemical communications.

[35]  S. Bhattacharya,et al.  First report of Zn2+ sensing exclusively at mesoscopic interfaces. , 2003, Chemical communications.

[36]  V. Aswal,et al.  Role of different counterions and size of micelle in concentration dependence micellar structure of ionic surfactants , 2003 .

[37]  V. Aswal,et al.  Dependence of the size of micelles on the salt effect in ionic micellar solutions , 2002 .

[38]  Kevin Barraclough,et al.  I and i , 2001, BMJ : British Medical Journal.

[39]  A. Gräslund,et al.  The position of the cell penetrating peptide penetratin in SDS micelles determined by NMR , 2001, FEBS letters.

[40]  G. Mancini,et al.  Role of Counterions in the Solubilization of Benzene by Cetyltrimethylammonium Aggregates. A Multinuclear NMR Investigation , 2000 .

[41]  I. Furó,et al.  Shape changes of C(16)TABr micelles on benzene solubilization , 1999 .

[42]  D. Reinhoudt,et al.  Neutral anion receptors: design and application , 1998 .

[43]  David N. Reinhoudt,et al.  Neutral anion receptors; synthesis and evaluation as sensing molecules in chemically modified field effect transistors (CHEMFETs) , 1997 .

[44]  D. Reinhoudt,et al.  UO2-salenes: neutral receptors for anions with a high selectivity for dihydrogen phosphate , 1992 .

[45]  C. A. Bunton,et al.  The binding of phenols and phenoxide ions to cationic micelles , 1988 .

[46]  D. Nicoli,et al.  Dynamic light scattering from cetyltrimethylammonium bromide micelles. Intermicellar interactions at low ionic strengths , 1982 .

[47]  F. Hattab,et al.  Fluoride in drinking water. , 1980, Community dentistry and oral epidemiology.

[48]  U. Henriksson,et al.  Nitrogen-14 nuclear magnetic relaxation in aqueous micellar solutions of n-hexadecyltrimethylammonium bromide and chloride , 1977 .

[49]  E. Duynstee,et al.  Organic Reactions Occurring in or on Micelles. I. Reaction Rate Studies of the Alkaline Fading of Triphenylmethane Dyes and Sulfonphthalein Indicators in the Presence of Detergent Salts1 , 1959 .