Supporting Information. Surface Functionalized Polystyrene Latexes using Itaconate based Surfmers
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1 Supporting Information Surface Functionalized Polystyrene Latexes using Itaconate based Surfmers Saheli Chakraborty and S Ramakrishnan* Department of Inorganic and Physical Chemistry Indian Institute of Science, Bangalore INDIA raman@iisc.ac.in Table of contents 1. Synthetic procedures for the preparation of surfmers S2-S3 2. Figure S1 LCST of C16-Ita-PEG350 S4 3. Figure S2 Variation of particle size with surfmer conc. S4 4. Derivation of relationship between surfmer conc. and emulsion particle size S5 5. Figure S3 Swelling studies of crosslinked PEGylated emulsions S6 6. Figure S4 NMR spectra of glyceryl PS emulsions S7 7. Figure S5 NMR spectra of Dopa functionalized PS emulsions S8 8. Figure S6 DLS data on Dopa functionalized emulsions S8 9. Figure S7 SEM images of silica particles adhering to Dopa-PS coated glass and PS particles on these silica-coated glass S9 10. Figure S8 NMR spectra of C16-Ita-F8 and styrene copolymers S Figure S9 Water contact angle measurements of PEGylated PS and fluorinated PS coated glass plates S11 S1
2 Synthesis of the surfmers Synthesis of C16-Ita-PEG g (9.8 mmol) of cetyl itaconate 1 was dissolved in 10 ml of dry DMSO and 1.2 g (14.7 mmol) of NaHCO3 was added to it. The mixture was stirred at 45 o C for 30 minutes. 5.3 g (10.6 mmol) of PEG350-tosylate was dissolved in 10 ml of dry DMSO and added to the reaction mixture. The solution was stirred at 45 o C for 4 days. After the reaction 100 ml of DCM was added to it and the organic layer was washed thoroughly with brine solution to remove the DMSO and finally it was passed through anhydrous Na2SO4 and evaporated to obtain the pure the product. Yield = 65% NMR (400 MHz, δ ppm, CDCl3): 0.87 (3H, t, -CH2CH3), 1.25 (26H, m, CH3-(CH2)13CH2), 1.61 (2H, m, -CH2-CH2COO), 3.33 (2H, s, COO-CH2-C), 3.37 (3H, s, -OCH3), (~26H, m, -OCH2CH2O-), 4.09 (2H, t, -CH2-CH2COO), 4.3 (2H, t, -OCH2CH2COO), 5.72 (1H, s, C=CHHˊ), 6.35 (1H, s, C=CHHˊ) Synthesis of C16-Ita-F8 Since 1-iodo-1H,1H,2H,2H perfluorodecane was extremely unreactive towards neucleophilic substitution, the esterification was performed by making acid chloride of the cetyl itaconate. 1 g (2.8 mmol) of cetyl itaconate was dissolved in 10 ml dry DCM. 250 micro-litres (4.2 mmol) of oxalyl chloride was added to the reaction mixture along with a drop of DMF. The reaction was carried out at room temperature for 4 hours. After that 1.5 g (3.2 mmol) of 1H,1H,2H,2Hperfluorodecanol was added to it along with 370 micro-litres (4.2 mmol) pyridine, and the solution was heated at 50 o C for ~12 h. The organic layer was then washed with 1N HCl, then passed through anhydrous Na2SO4 and concentrated using a rotary evaporator. The solid residue thus obtained was recrystallized twice from methanol to obtain pure product. Yield = 60% NMR (400 MHz, δ ppm, CDCl3): 0.87 (3H, t, -CH2CH3), 1.25 (26H, m, CH3-(CH2)13CH2), 1.61 (2H, m, -CH2-CH2COO), 2.50 (2H,m, CH2CH2(CF2)7) 3.33 (2H, s, COO-CH2-C), 4.07 (2H, t, -CH2-CH2COO), 4.47 (2H,t, -COOCH2CH2(CF2)7), 5.75 (1H, s, C=CHHˊ), 6.34 (1H, s, C=CHHˊ) S2
3 Synthesis of C8-Ita-Gly 2 g (8.2 mmol) of cetyl itaconate and 4 g (49 mmol) glycidol was taken in dry toluene and refluxed for 5 hours in presence of 48 mg (5 mol%) p-tsa. Pure product was obtained by column purification of the crude (PET ether/ EtOAc - 3:1) product. Yield 50% NMR (400 MHz, δ ppm, CDCl3): 0.87 (3H, t, -CH2CH3), 1.25 (10H, m, CH3-(CH2)5CH2), 1.61 (2H, m, -CH2-CH2COO), 3.33 (2H, s, COO-CH2-C), (1H, m, - CH2CH(OH)CH2OH), 4.10 (2H, t, -CH2CH(OH)CH2OH), (2H, m, - CH2CH(OH)CH2OH), 5.75 (1H, s, C=CHHˊ), 6.34 (1H, s, C=CHHˊ) Synthesis of C8-Ita-Dopa 940 mg of dopamine (4.9 mmol) was dissolved in 10 ml of dry DMF in presence of 600 µl triethyl amine. The reaction mixture was cooled in an ice bath. To the cooled reaction mixture 1 g of octyl itaconate (4.1 mmol), 940 mg of EDC.HCl (5.3 mmol) and 60 mg of (0.4 mmol) hydroxybenzyltriazole (HOBT) was added and the solution was stirred at room temperature under N2 atmosphere for next 24 h. Thereafter, 1 N HCl was added to the reaction mixture and the solution was extracted in 50 ml DCM. The organic layer was passed through anhydrous Na2SO4 and finally evaporated to obtain brown coloured semi-solid. Pure product was obtained by column purification using PET/EtOAC (1:1). NMR (400 MHz, δ ppm, CDCl3): 0.88 (3H, t, -CH2CH3), 1.25 (26H, m, CH3-(CH2)5CH2), 1.61 (2H, m, -CH2-CH2COO), 2.74 (2H, t, Ph-CH2CH2NH-), 3.33 (2H, s, COO-CH2-C), 3.5 (2H, q, Ph-CH2CH2NH-), 4.1 (2H, t, -COOCH2(CH2)6CH3), 5.37 (1H, s, Ph-CH2CH2NH- ), 5.74 (1H, s, C=CHHˊ), 6.51 (2H, d, PhH(A,B)), 6.76 (1H, s, C=CHHˊ), 6.82 (1H, d, PhH(C)) S3
4 Particle size from DLS (nm) Particle size from DLS (nm) % Transmittance Heating Cooling Temperature ( o C) Figure S1. Determination of LCST of C16-Ita-PEG350; a plot of percent transmittance of the solution (5 wt% in water) at 600 nm (where the sample has no absorbance) as function of temperature that clearly reveals the sudden decrease in transmittance at the LCST mole% of surfactant (mol% of surfactant) -1 Figure S2. A plot of variation of particle size with the amount of surfmer, measured using DLS (left). Plot showing the inverse relationship between size and surfmer concentration (right). S4
5 Derivation of the relationship between surfmer concentration and emulsion particle size Let us consider that a droplet of volume V and radius R is broken down into n number of droplets, each of volume Vn and radius Rn. Therefore, V = nvn Or, 4/3 π R 3 = n x 4/3 π Rn 3 Implies that: n = (R/Rn) 3 Considering that the total surface area of the newly formed droplets is given by An An = n x 4πRn 2 = (R/Rn) 3 x 4πRn 2 = (R 3 x 4π) / Rn ; An = 4π R 3 /Rn Which implies that: RnAn = 4π R 3, which implies that for a given volume of the dispersed phase (in this case styrene), RnAn = constant. Since, the surfmer resides at the interface of the emulsion droplet, the total surface area (An) is proportional to the total concentration of the surfmer with respect to the dispersed phase, styrene. Thus, the size (Rn) would be inversely proportional to the surfmer concentration; hence, a plot of size versus the inverse of surfmer concentration should give a straight line (see Figure S2). S5
6 Swelling studies of PEGylated crosslinked PS emulsion particles Figure S3A. DLS of the PS emulsion (PS-10), cross-linked PS emulsion (PS-10-1X) and of solvent (CHCl3) swollen crosslinked emulsion. Firstly, it is seen that 1 mole-percent divinyl benzene does not influence the particle size significantly, provided the surfmer concentration is kept constant here at 10 mole-percent with respect to the monomer; suggesting that crosslinking does not affect the particle size. The swelling of the emulsion particles (20μL of CHCl3 was added to 2 ml of the aqueous emulsion) results in a bimodal distribution of particle sizes some particles evidently have taken up considerably more chloroform than others. Figure S3B. Swelling experiment with a water-soluble organic solvent, methyl ethyl ketone (MEK) lead to less swelling and also more uniform swelling, yielding a monomodal distribution of particle sizes. (50μL of MEK was added to 2 ml of the aqueous emulsion). S6
7 Glyceryl functionalized PS emulsions PS-Gly-20 PS-20-glycerol PS-15-glycerol PS-Gly-15 PS-10-glycerol PS-Gly ppm Figure S4. NMR spectral stack plot of the reprecipitated polystyrene latexes prepared using C8-Ita-Gly. The highlighted region indicates the terminal -CH3 of the surfmer, which was used for the determination of copolymer composition. S7
8 Dopa-functionalized PS emulsions using C8-Ita-Dopa ppm Figure S5. NMR spectra of the purified PS latex prepared using 20 mole % of the surfmer, C8- Ita-Dopa. Here again, the terminal CH3 group of the cetyl chain was used to estimate the surfmer incorporation. Entry Feed ratio (Surf : styrene) in mol Surf - styrene ratio in NMR % conversion Amount of coagulum DLS (nm) M n (Daltons) PS-Dopa-20 1:5 1:6 80% Table T1. Recipe of emulsion polymerization with dopamine containing surfmer. Figure S6. DLS of the dopamine coated latex indicating the formation of uniform sized particles with a average diameter of 145 nm. S8
9 Figure S7A. Left: SEM image of SiO2 nanoparticles that has adhered onto a glass substrate that was first been treated with dopa-functionalized PS emulsions particles (SEM image of the treated glass in the main manuscript; Figure 8); the locations where SiO2 nanoparticles have adhered are the locations below which the dopa-functionalized PS particles are present. Right: an unmodified glass plate is seen to pick up no SiO2 nanoparticles. These experiments were done by simple dipping of the substrate into the aq. emulsion for a period of 48 h, after which it was rinsed in water under ultrasonication for 15 secs. Figure S7B. SEM image dopa-functionalized PS latex particles adhered onto the TiO2 coated Si surface; the adhesion happens by simple dipping of the substrate into the aq. emulsion for a period of 48 h, after which it was rinsed in water under ultrasonication for 15 secs. SiO 2 SiO 2 SiO 2 SiO 2 Scheme S1. Schematic representation of the process that leads to the adhesion of SiO2 particles onto the modified glass surface. S9
10 Emulsion polymerization using fluorous sufmer, C16-Ita-F8 Entry Feed ratio (Surf : styrene) in mol Surf - styrene ratio in NMR % conversion Amount of coagulum M n (Daltons) PS-F8-3 1:35 1:35 90% Coagulated PS-F8-5 1:20 1:8 65% Coagulated PS-F8-10 1:10 1:4 65% Coagulated PS-F8-20 1:5 1:1 55% Coagulated Table 2. Recipe for the emulsion polymerization of styrene in a fluorous solvent, NOVEC 3500, using C16-Ita-F8 as surfmer. In all cases, no stable emulsion was generated; however, the coagulated polymer was soluble and was purified to yield styrene-itaconate copolymers. PS-F8-20 PS-F8-10 PS-F8-5 PS-F ppm Figure S8. Proton NMR spectral stack plot of the reprecipitated polystyrene latexes using C16- Ita-F8; the highlighted region shows the terminal -CH3 of the surfmer, and was used to estimate the copolymer composition. S10
11 72 o 124 o PEGylated PS Fluorinated PS Figure S9. Water contact angle measurements on glass surfaces coated with the PS-PEG-15 and PS-F8-10; the compositions of the copolymers were selected such that in both cases the ratio of Sty:surfmer is roughly similar (1:5 in the former and 1:4 in the latter). References Chakraborty, S.; Ramkumar, S. G.; Ramakrishnan, S. Macromolecules 2017, 50, 5004 S11
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