revised esi 0807 - rsc.org · as a viscous liquid. c16me (3.0 g, 7.23 mmol) and 18 ml 1n naoh (18...

Supplementary Information Recovery and Redispersion of Gold Nanoparticles Using a Self-assembly of pH Sensitive Zwitterionic Amphiphile Clara Morita-Imura*, Yoshiro Imura, Takeshi Kawai and Hitoshi Shindo* Department of Applied Chemistry, Chuo University Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan) *[email protected], [email protected] Synthesis of C16CA Methyl acrylate (14.30 g, 0.17 mol) was added to hexadecylamine (2.0 g, 8.30 mmol) in 15 mL methanol. The solution was stirred at 40°C for 3 days followed by removal of the solvents and excess methyl acrylate by rotary evaporation to yield 3-[(2-methoxycarbonyl-ethyl)-hexadecyl-amino]-propionic acid methyl ester (C16ME) as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol and the mixture stirred for 1 day at room temperature. Removal of the solvent by evaporation yielded 3-[(2-carboxy-ethyl)-hexadecyl-amino]-propionic acid as a white solid, which was washed with hexane and methanol (yield: 90%). 1 H NMR (D 2 O): δ 0.88 (t, 3H, CH 3 ), 1.25 (br, 28H, CH 2 ), 1.45 (br, 4H, CH 2 CH 3 , CH 2 CH 2 CH 2 N), 2.36 (t, 4H, CH 2 CH 2 CO), 2.42 (t, 2H, CH 2 N), 2.73 (t, 4H, NCH 2 CH 2 CO) The Krafft point of C18AA was 7°C, which was obtained using a DSC 8000 instrument (Perkin Elmer). The pKa value was determined by acid-base titration using a pH meter (Horiba) with 0.1 N HCl and 0.1 N NaOH aqueous solutions. The pKa was 6.2, 1.6, 2.0 at 27°C. Scheme S1. Synthesis of 3-[(2-carboxy-ethyl)-hexadecyl-amino]-propionic acid (C16CA). Electronic Supplementary Material (ESI) for ChemComm. This journal is © The Royal Society of Chemistry 2014

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Page 1: Revised ESI 0807 - rsc.org · as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol and the mixture stirred for 1 day at room temperature

Supplementary Information

Recovery and Redispersion of Gold Nanoparticles Using a Self-assembly of pH

Sensitive Zwitterionic Amphiphile

Clara Morita-Imura*, Yoshiro Imura, Takeshi Kawai and Hitoshi Shindo*

Department of Applied Chemistry, Chuo University

Kasuga, Bunkyo-ku, Tokyo 112-8551 (Japan)

*[email protected], [email protected]

Synthesis of C16CA

Methyl acrylate (14.30 g, 0.17 mol) was added to hexadecylamine (2.0 g, 8.30 mmol) in 15 mL methanol.

The solution was stirred at 40°C for 3 days followed by removal of the solvents and excess methyl acrylate by

rotary evaporation to yield 3-[(2-methoxycarbonyl-ethyl)-hexadecyl-amino]-propionic acid methyl ester (C16ME)

as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol

and the mixture stirred for 1 day at room temperature. Removal of the solvent by evaporation yielded

3-[(2-carboxy-ethyl)-hexadecyl-amino]-propionic acid as a white solid, which was washed with hexane and

methanol (yield: 90%).

1H NMR (D2O): δ 0.88 (t, 3H, CH3), 1.25 (br, 28H, CH2), 1.45 (br, 4H, CH2CH3, CH2CH2CH2N), 2.36 (t, 4H,

CH2CH2CO), 2.42 (t, 2H, CH2N), 2.73 (t, 4H, NCH2CH2CO)

The Krafft point of C18AA was 7°C, which was obtained using a DSC 8000 instrument (Perkin Elmer).

The pKa value was determined by acid-base titration using a pH meter (Horiba) with 0.1 N HCl and 0.1 N NaOH

aqueous solutions. The pKa was 6.2, 1.6, 2.0 at 27°C.

Scheme S1. Synthesis of 3-[(2-carboxy-ethyl)-hexadecyl-amino]-propionic acid (C16CA).

Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2014

Page 2: Revised ESI 0807 - rsc.org · as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol and the mixture stirred for 1 day at room temperature

Rheological measurements

Figure S1 (a) Steady shear viscosity measurement, (b) dynamic viscoelastic measurement of 6 wt% C16CA

solution at pH 1.

Preparation of Au NPs capped with citric acid

0.09 g of citric acid was dissolved in 20 mL of purified water. 80 mL of 0.625 mM aqueous

HAuCl4 solution and 20 mL of 15 mM aqueous citric acid solution were mixed at 90°C and stirred

for 10 min to obtain a reddish colored solution. The solution was stirred for 1 day at room

temperature.

Figure S2. (a) UV-Vis spectra of Au NPs dispersion as prepared. (b) TEM image of Au NPs as prepared.

Page 3: Revised ESI 0807 - rsc.org · as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol and the mixture stirred for 1 day at room temperature

Redispersion of Au NPs

Figure S3 TEM images of redispersion of Au NPs at [C16CA]/[Au] = (a) 100, (b) 80, (c) 50, (d) 20 and (e) 10.

Figure S4 Distributions of Au NPs for (a) initial dispersion and (b-f) redispersions at various [C16CA]/[Au] ratios.

Page 4: Revised ESI 0807 - rsc.org · as a viscous liquid. C16ME (3.0 g, 7.23 mmol) and 18 mL 1N NaOH (18 mmol) were added to 18 mL methanol and the mixture stirred for 1 day at room temperature

Figure S5. TEM images of multicycled redispersion of Au NPs at (a) redispersion-1 (cycle 1), (b) redispersion-2

(cycle 2) and (c) redispersion-3 (cycle 3).

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