A Selective Fluoride Sensor Derived from Imine-Phenol Derivative
Abstract
Anion sensor, 2-((E)-((2-hydroxyphenyl)imino)methyl)-2-((E)-phenyldiazenyl)phenol (L) bearing a 2-iminephenol group as a binding unit and a phenylazo group as a signaling unit was synthesized in high yield by two simple steps. Complexations of sensor L with various anions were carried out by UV-visible spectrophotometry in acetonitrile solvent. The results indicated that the sensor L showed high selectivity for fluoride over other anions (F->>> CH3COO->H2PO4-). The pale yellow solution was observed to have turned dark yellow in color with a new band at 468.5 nm. The stoichiometry of complex between L and F- was 1:2 while the stoichiometries of complexes between L and CH3COO- or H2PO4- were 1:1. The association constants of L towards F-, CH3COO- and H2PO4- were calculated to be (1.89±0.12) x 108 M-2, (3.50±0.28) x 104 M-1 and (2.67±0.40) x 104 M-1, respectively using the UV-visible titration data. The presence of hydrogen bonding interaction between L and F- was confirmed by 1H NMR titration results which displayed deprotonation of the OH proton of phenol. Furthermore, the interaction between L and anions were evaluated by computational chemistry using B3LYP/6-31G(d,p) level of calculation. The results confirmed that the formation between L and anion are 1:2 for F- and 1:1 for CH3COO- and H2PO4-. The binding energies are -144.59, -37.30 and -31.71 kcal/mol for L-F-, L-CH3COO- and L- H2PO4- systems, respectively. The calculation is in a relatively good agreement with the experimental results. Keyword: Anion sensor, Fluoride, Hydrogen bond, Computational ChemistryReferences
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Tavallali, H., Rad, G.D., Parhami, A., & Abbasiyan, E. (2012). A New Application of Bromopyrogallol Red as A
Selective and Sensitive Competition Assay for Recognition and Determination of Acetate Anion in DMSO/Water Media. Dyes and Pigments, 94, 541-547.
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nitrophenyl)]ditthiourea. Srinakharinwirot Science Journal, 29, 32-46. (in Thai)
Zimmermann-Dimer, L.M., & Machado, V.G. (2009). Chromogenic Anionic Chemosensors Based on Protonated
Merocyanine Solvatochromic Dyes: Influence of the Medium on the Quantitative and Naked-eye
Selective Detectin of Anionic Species. Dyes and Pigments, 82, 187-195.
Receptors. Accounts of Chemical Research, 39, 343-353.
Boiocchi, M., Boca, L.D., Gómez, D.E., Fabbrizzi, L., Licchelli, M., & Monzani, E. (2004). Nature of Urea-Fluoride
Interaction: Incipient and Definitive Proton Transfer. Journal of the American Chemical Society, 126, 16507-16514.
Chen, C-F., & Chen, Q-Y. (2004). A Tetra-sulfonamide Derivative Bearing Two Dansyl Groups Designed as A
New Fluoride Selective Fluorescent Chemosensor. Tetrahedron Letters, 45, 3957-3960.
Dalapati, S., Alam, M.A., Jana, S., & Guchhait, N. (2011). Naked-eye Detection of F- and AcO- Ions by Schiff Base
Receptor. Journal of Fluorine Chemistry, 132, 536-540.
Davaraj, S., Saravanakumar, D., & Kandaswamy, M. (2009). Dual Responsive Chemosensors for Anion and
Cation: Synthesis and Studies of Selective Chemosensor for F- and Cu(II) Ions. Sensors and Actuators B,
136, 13-19.
Esteban-Go´mez, D., Fabbrizzi, L., & Licchelli, M. (2005). Why, on Interaction of Urea-Based Receptors with
Fluoride, Beautiful Colors Develop. The Journal of Organic Chemistry, 70, 5717-5720.
Ghosh, K., & Adhikari, S. (2006). Colorimetric and Fluorescence Sensing of Anions Using Thiourea Based
Coumarin Receptors. Tetrahedron Letters, 47, 8165-8169.
Gunnlangsson, T., Kruger, P. E., Jensen, P., Tierney, J., Ali, H.D.P., & Hussey, G.M. (2005). Colorimetric “Naked
Eye” Sensing of Anions in Aqueous Solution. Journal of Organic Chemistry, 70, 10875-10878.
Gunnlaugsson, T., Kruger, P.E., Lee, T.C., Parkesh, R., Pfeffer, F.M., & Hussey, G.M. (2003). Dual Responsive
Chemosensors for Anions: The Combination of Fluorescent PET (Photoinduced Electron Transfer) and Colorimetric Chemosensors in A Single Molecule. Tetrahedron Letters, 44, 6575-6578.
Hijji, Y. M., Barare, B., Kennedy, A.P., & Butcher, R. (2009). Synthesis and Photophysical Characterization of A
Schiff Base as Anion Sensor. Sensors and Actuators B, 136, 297-302.
Hong, S-J., & Lee, C-H. (2012). Nitrovinyl Substituted Calix[4]pyrrole as A Unique, Reaction-Based
Chemosensor for Cyanide Anion. Tetrahedron Letters, 53, 3119-3122.
Hoop, M.A.G.T., Cleven, R.F.M.J., Staden, J.J.V., & Neele, J. (1996). Analysis of Fluoride in Rain Water
Comparison of Capillary Electrophoresis with Ion Chromatography and Ion-Selective Electrode Potentiometry. Journal of Chromatography A, 739, 241-248.
Kaewtong, C. (2010). Supramolecular Chemistry; Cation and Anion Sensors. Science Journal Ubon Ratchathani
University, 52-59. (in Thai)
Kondo, S-I., Suzuki, T., & Yano, Y. (2002). Effect of Hydroxyl Groups in Receptors Bearing Disulfonamide
on Anion Recognition in Acetonitrile-d3. Tetrahedron Letters, 43, 7059-7061.
Muensri, P., Tongraung, P., Pingaew, R., Pumsa-ard, K., & Jittangprasert, P. (2013). Synthesis of Bissulfonamide
Derivative for Fluoride Sensor. Srinakharinwirot Science Journal, 29, 83-94. (in Thai)
Refat, M.S., El-Deen, I.M., Amin, R.R., & El-Ghol, S. (2010). Spectroscopic Studies and Biological Evaluation of
Some Transition Metal Complex of A Novel Schiff Base Ligands Derived From 5-arylazo-salicyladehtde and o-aminophenol. Toxicological and Environmental Chemistry, 92, 1093-1110.
Shao, J. (2010). A Novel Colorimetric and Fluorescence Anion Sensor with a Urea Group as Binding and
a Coumarin Group as Signal Unit. Dyes and Pigments, 87, 272-276.
Shao, J., Qiao, Y-H., Lin, H.,& Lin, H-K.(2008). A Turn-On Fluorescent Anion Receptor Based on N,N’-di- -
Naphthyl-1,10-phenanthroline-2,9-diamide. Journal of Luminescence, 128, 1985-1988.
Tavallali, H., Rad, G.D., Parhami, A., & Abbasiyan, E. (2012). A New Application of Bromopyrogallol Red as A
Selective and Sensitive Competition Assay for Recognition and Determination of Acetate Anion in DMSO/Water Media. Dyes and Pigments, 94, 541-547.
Tongraung P., Pansanit, A., Yuanboonlim, W., & Tiyasri, S. (2007). Anion Sensing by N,N-(m-xylylene)-bis-[N-(p-
nitrophenyl)]ditthiourea. Srinakharinwirot Science Journal, 29, 32-46. (in Thai)
Zimmermann-Dimer, L.M., & Machado, V.G. (2009). Chromogenic Anionic Chemosensors Based on Protonated
Merocyanine Solvatochromic Dyes: Influence of the Medium on the Quantitative and Naked-eye
Selective Detectin of Anionic Species. Dyes and Pigments, 82, 187-195.
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2016-06-21
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