Supporting Information
Synthesis of decylphosphonic acid. Decylphosphonic acid was prepared by the Michaelis-Arbuzov
reaction followed by an acid hydrolysis of the corresponding ester phosphonate. Decylbromide (5mL,
0.024 mol) and an excess of triethylphosphite (15mL, 0.087mol) were refluxed with a nitrogen stream
bubbling into the solution at 150°C for 24h. The solution was cooled, and then 55mL of water was added
in one portion. The two-phase mixture was stirred for 3h and extracted with chloroform (40ml). The
organic phase, washed with saturated NaCl is then dried over MgSO4. The filtered solution was
concentrated by rotary evaporation to give diethyldecylphosphonate, as yellow oil. Subsequently, this
ester was hydrolysed by heating under reflux at 100°C with concentrated HCl (200ml) for 12h to yield
decylphosphonic acid as a white precipitate upon cooling. DPA was purified by recrystallization with
hexane. 1H NMR (400 MHz, CDCl3):  0.880 (t, 3H, C10), 1.258-1.362 (m, 14H, C3-C9), 1.607-1.736 (m, 4H,
C1-C2), 11.255 (s, 2H, PO(OH)2);
C NMR (100 MHz, CDCl3):  14.111 (s, CH3-CH2), 22.083 (d,
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CH2CH2PO(OH)2, J2CP = 4.9 Hz), 22.685 (s, CH2), 26.153 (d, CH2PO(OH)2, J1CP = 144 Hz), 29.100-29.578 (4s,
CH2), 30.596 (d, CH2CH2CH2PO(OH)2, J3CP = 17 Hz), 31.903 (s, CH2).
Experimental procedure for the synthesis of standard HCl doped polyaniline
PANI doped with HCl was synthesized by the slow addition, under stirring of 50 ml of a 1M HCl aqueous
solution of ammonium peroxydisulfate (25 mmol) to 50 ml of a 1M HCl aqueous solution of aniline (20
mmol).
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Table S1. Solubility (mg/ml) of DPA and HCl doped PANI in some common organic solvents
Sample
Solvent
Chloroform
Toluene
n-heptane
Ethanol
ES-1,25-1
3.58
2.56
1.90
2.00
ES-1,25-1,5
3.89
2.88
1.82
2.21
ES-1,25-2,5
4.04
3.08
2.24
2.35
ES-1,25-5
4.57
3.46
2.62
2.55
PANI-HCl
0.72
0.66
0.56
0.50
2
10 µm
Figure S1. Light micrograph of 3.79 mM DPA dispersed in water taken at room temperature.
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(A)
48 h
24 h
600 min
580 min
560 min
540 min
480 min
0 min
(B)
48 h
24 h
540 min
420 min
360 min
300 min
240 min
0 min
Figure S2. UV-vis spectra of (a) ES-1.25-2.5 and (b) ES-1.25-1.5 dispersions recorded during
polymerization and color changes of reaction mixture.
4
1,2
1
ES-1.25-1.5
0,8
Absorbance
ES-1.25-2.5
ES-1.25-5
0,6
0,4
0,2
0
0
100
200
300
400
500
600
700
800
Polymerization time / min
Figure S3. Changes in the absorbance of the polaron band at 680-750 nm with respect to polymerization
time
Viscosity(mPa.s)
12
8
4
0
1
1.5
2
2.5
3
3.5
4
4.5
5
[DcPA]/[An]
FigureS4. Viscosity of the initial DPA micellar medium as a function of DPA/aniline molar ratio
5
1484
1578
815
1375
Y =5
Absorbance
Y =2.5
Y=1.5
1040
Y=1
1700
1500
1300
1100
900
700
500
Wavenumber, cm-1
Figure S5. FTIR spectra of the dedoped PANIs in the region between 500 and 1700 cm -1 with Y=
DPA/aniline molar ratio in the feed.
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0,6
Fe concentration (ppm)
0,5
0,4
0,3
0,2
0,1
0
PVB
PANI EB 2%/PVB PANI-HCl 2%/PVB
ES-0.5-2.5/PVB
Figure S6. Iron concentration after 10 days immersion test in 3.5% NaCl solution
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