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1 Supporting Information Mop up the Oil, Metal and Fluoride Ions from Water Tanmay Das a and Debasish Haldar a * a Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur, West Bengal , India, Fax: (+) ; Tel: ; deba_h76@yahoo.com; deba_h76@iiserkol.ac.in Table of contents 1. Supporting information Figure S1 and S Supporting information Figure S3 and S Supporting information Figure S5 and S Supporting information Figure S7 and S Supporting information Figure S9 and S Supporting information Figure S Figure S12, Absorption spectra of 1 with metal ions 7 8. Figure S13, emission spectra of 1 with anions 8 9. Figure S14, emission of 1 with fluoride Figure S15, S16, Absorption spectra of water before and after purification Figure S17 Absorption spectra of water before and after purification Binding constant and detection limit calculation Breakthrough experiment Sorption isotherm and sorption kinetics Legends for video 1, 2, 3 and 4 12 S1
2 ESI Figure S1. (a) Change of absorption spectra of 1 with gradual addition of Cu 2+ ion (aqueous CuSO 4.5H 2 O solution), (b) Fluorescence quenching of 1 with gradual addition of Cu 2+ ion (aqueous CuSO 4.5H 2 O solution). ESI Figure S2. Job's plot for 2:1 complexation of 1 with Fe 3+ in methanol. (a) Absorption spectra for all ten sets where the total concentration of 1 and Fe 3+ was kept constant at 100 µm, (b) Plot of absorbance at 405 nm vs mole fraction of Fe 3+ ion. S2
3 [Fe] (ppb) Time (min) ESI Figure S3. Fe 3+ sorption kinetics of 1 with Fe 3+ initial concentration of 100 ppm at a V/m ratio of 1333 ml g -1. ESI Figure S4. Job's plot for 1:1 complexation of 1 with F - in dichloromethane. (a) Absorption spectra for all ten sets where the total concentration of 1 and F - was kept constant at 125 µm, (b) Plot of absorbance at 437 nm vs mole fraction of F - ion. S3
4 ESI Figure S5. Change of Absorption spectra of 4 with gradual addition of trifluoroacetic acid. ESI Figure S6. (a) Benesi-Hildebrand plot for determining the binding constant of 1 with F - ion (in THF, ph = 7.0) at 298 K. The binding constant value is 2.55 X 10 5 M -1. (b) Normalized fluorescence intensity of 1 (3.9 µm) at each concentration of F - (THF, ph = 7.0) at 298 K. A linear curve was obtained from these normalized fluorescence intensity data. The detection limit obtained was 6.76 X 10-7 M i.e ppb. S4
5 ESI Figure S7. Detection of fluoride ion present in water. Addition of 100 µl of 1 ppm aqueous fluoride solution to the THF solution of 1 (1.21 x 10-6 M) causes complete quenching of fluorescence. 60 Adsorbed F - (mg/g) Number of Cycles ESI Figure S8. Fluoride uptake capacity in consecutive cycles after regeneration of compound 1. S5
6 ESI Figure S9. FESEM images of normal sponge (a), (c) and compound 1 coated sponge (b), (d). S6
7 ESI Figure S10. Oil spill removal from the surface of the water. ESI Figure S11. Oil spill removal from the bottom of the water. Figure S12. Absorption spectra of 1 in methanol upon addition of aqueous solution of different metal ions (10 eq). S7
8 Figure S13. (a) Emission spectra of 1 in presence of 1 equivalent of different anions, (b) Ratio of fluorescence intensities before addition of anion and after addition of anion. Figure S14. Effect on fluorescence emission of compound 1 after treating (a) polluted fluoride containing water and (b) same fluoride containing water after treatment. S8
9 Figure S15. Absorption Spectra of (a) Fe 3+, (b) Hg 2+, (c) Mn 2+ and (d) Ni 2+ ion containing water before and after purification. Figure S16. Absorption Spectra of (a) Co 2+, (b) Cd 2+, (c) Cr 3+ and (d) Cu 2+ ion containing water before and after purification. S9
10 Figure S17. Absorption Spectra of (a) Zn 2+ and (b) Pb 2+ ion containing water before and after purification. Determination of the binding constant: The binding constant was calculated from the fluorescence titration experiment using the following modified Benesi Hildebrand equation: [1] 1/ F i -F min = 1/( F max -F min ) + (1/K[F - ]){1/ (F max -F min )}. Here F min, F i, F max are the fluorescence intensities of 1 in the absence of F -, at an intermediate F - concentration and at the maximum F - concentration respectively. K is the binding constant, [F - ] is the concentration of F -. From the Plot of (F max -F min )/ (F i -F min ) against [F - ] -1 for 1, the value of K (±6.8%) obtained from the slope is 2.55 X 10 5 M -1. Determination of the detection limit: The detection limit for the F - was determined from the fluorescence titration experiment following the reported method. [2] The fluorescence intensity values were normalized at the emission maxima between the minimum intensity found at zero equivalents of F - and the maximum enhanced intensity on addition of F -. A linear curve was obtained by plotting (F min -F i )/ (F min -F max ) vs log[f - ]. The detection limit obtained by the extrapolation of the straight line on the x axis is 676 nm. Breakthrough experiment: Three hundred milligrams of compound 1 was packed into a pipette (inner diameter of 3.0 mm) to form an adsorption column and the packed sample length was about 5 cm. An aqueous solution (50 ml) containing Pb(NO 3 ) 2, FeCl 3, Cd(NO 3 ) 2, Hg(NO 3 ) 2, NaCl, Cu(NO 3 ) 2 and KBr each having a concentration of about 5 ppm was then passed through the column and the filtrates were analyzed using ICP-MS to determine residual metal ions concentrations. S10
11 Cd 2+ sorption isotherm: 1 (50.0 mg) was added to each Erlenmeyer flask containing Cd(NO3) 2 solution (50 ml) with different concentrations. The mixtures were sonicated at room temperature for 2 h, and then were filtered separately through a Whatman 42.5 mm filter paper and the filtrates were analysed by using ICP-MS to determine the remaining Cd 2+ content. Cd 2+ sorption kinetics: 200 ml 48.7 ppm Cd 2+ aqueous solution and 100 mg compound 1 were added in an Erlenmeyer flask. Then the mixture was placed in a sonicator. 4 ml water sample was collected after 5 minutes interval from the starting point and then filtered using Whatman 42.5 mm filter paper. After filtration these samples were analyzed by ICP-MS. Fe 3+ sorption kinetics: 200 ml 100 ppm Fe 3+ aqueous solution and 180 mg compound 1 were added in an Erlenmeyer flask. Then the mixture was placed in a sonicator. 4 ml water sample was collected after 5 minutes interval from the starting point and then filtered using Whatman 42.5 mm filter paper. After filtration these samples were analyzed by ICP-MS. F - sorption kinetics: 200 ml 30 ppm F - aqueous solution and 200 mg compound 1 were added in an Erlenmeyer flask. Then the mixture was placed in a sonicator. 4 ml water sample was collected after 5 minutes interval from the starting point and then filtered using Whatman 42.5 mm filter paper. After filtration these samples were analyzed by fluorescence spectroscopy. In each case the percentage removal was calculated using the following equation: Percentage removal (%) = 100 X (C 0 -C t )/C 0 Distribution coefficient (K d ) value which is used to measure the affinity between the adsorbent and the ion, has been calculated using the equation: K d = {(C i -C e )/C e } x (V/m) Here V is the volume of the treated water (ml), m is the amount of the adsorbent, C i is the initial concentration and C e is the equilibrium concentration of the ion. S11
12 F - sorption isotherm: Compound 1 (50.0 mg) was added to each Erlenmeyer flask containing tetrabutylammonium fluoride (TBAF) solution (50 ml) with different concentrations. The mixtures were sonicated at room temperature for 2 h, and then were filtered separately through a Whatman 42.5 mm membrane filter, and the filtrates were analyzed by fluorescence spectroscopy to determine the remaining F - contentration. Supplementary video 1. Sonication based purification of metal ion containing waste water. Addition of compound 1 in aqueous Fe 3+ solution followed by sonication provides clean water. Supplementary video 2. Oil spill removal from the surface of water. Removal of mustard oil using highly hydrophobic polystyrene sponge coated with compound 1. Supplementary video 3. Removal of heavier organic solvents from the bottom of water. Removal of chloromethane using highly hydrophobic polystyrene sponge coated with compound 1. Supplementary video 4. Removal of oil spill from water surface using suction pump. Removal of mustard oil with highly hydrophobic polystyrene sponge coated with compound 1 using a suction pump. References (1) Ahamed, B. N.; Ravikumar, I.; Ghosh, P. A new chemosensor that signals Hg(II), Cu(II) and Zn(II) at different emission wavelengths: selectivity toward Hg(II) in acetonitrile. New J. Chem. 2009, 33, (2) Caballero, A.; Martínez, R.; Lloveras, V.; Ratera, I.; Vidal- Gancedo, J.; Wurst, K.; Tárraga, A.; Molina, P.; Veciana, J. Highly Selective Chromogenic and Redox or Fluorescent Sensors of Hg 2+ in Aqueous Environment Based on 1,4-Disubstituted Azines. J. Am. Chem. Soc. 2005, 127, S12
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