Supplemental Information
Synthesis and Solution Properties of a Double-tailed Quaternary Ammonium
Surfactant with a Protrudent Head Group
Binglei Songa,*, Zonghui Xua, Xiaona Yua, Shuyi Chena,
Shunan Lia, Rongzhen Shib, Zhenggang Cuia
a
The Key Laboratory of Food Colloids and Biotechnology, Ministry of Education,
School of Chemical and Material Engineering, Jiangnan University, Wuxi, Jiangsu
214122, PR China
b
School of Environmental and Chemical Engineering, Shanghai University, Shanghai
200444, PR China
Synthesis
The synthesis of dioctyldimethylammonium bromide (8-8)
N,N-dimethyloctylamine (20g, 0.127mol), 1-bromooctane (30g, 0.155mol) and
200mL acetone were mixed. The reaction was carried out at 70°C for 48 hours. The
acetone was then removed under reduced pressure and the residue was washed with
ethyl ether and petroleum ether six times. After dried under vacuum at 45°C for two
days, the final product obtained was gel-like solid. Yield: 20.3%.
1
H NMR (400 MHz, CDCl3) δ 3.52 (t, J = 8.0 Hz, 4H), 3.41 (s, 6H), 1.71 (s, 4H),
1.37-1.27 (m, 20H), 0.88 (t, J = 6.7 Hz, 6H).
Elemental analysis: Anal. Calcd. for C18H40BrNH2O: C, 58.68; H, 11.49; N, 3.80.
Found: C, 58.47; H, 11.75; N, 3.75.
The synthesis of didecyldimethylammonium bromide (10-10)
N,N-dimethyldecylamine (10g, 0.06mol), 1-bromodecane (13g, 0.067mol) and 100mL
acetone were mixed. The reaction was carried out at 70°C for 48 hours. The acetone
was then removed under reduced pressure. The residue was recrystallized with
petroleum ether three times. After dried under vacuum at 45°C for two days, the final
product obtained was white solid. Yield: 29%.
1
H NMR (400 MHz, CDCl3) δ 3.51 (t, J = 8.0 Hz, 4H), 3.42 (s, 6H), 1.70 (s, 4H),
1.36-1.26 (m, 28H), 0.88 (t, J = 6.8 Hz, 6H).
Elemental analysis: Anal. Calcd. for C22H48BrNH2O: C, 62.24; H, 11.87; N, 3.30.
Found: C, 61.95; H, 11.92; N, 3.11.
The synthesis of didodecyldimethylammonium bromide (12-12)
N,N-dimethyldodecylamine (10g, 0.045mol), 1-bromodecane (12g, 0.05mol) and
100mL acetone were mixed. The reaction was carried out at 70°C for 48 hours. The
acetone was then removed under reduced pressure. The residue was recrystallized
with petroleum ether three times. After dried under vacuum at 45°C for two days, the
final product obtained was white solid. Yield: 58%.
1
H NMR (400 MHz, CDCl3) δ 3.52 (t, J = 8.6 Hz, 4H), 3.42 (s, 6H), 1.70 (s, 4H),
1.36-1.26 (m, 36H), 0.88 (t, J = 6.8 Hz, 6H).
Elemental analysis: Anal. Calcd. for C26H56BrN: C, 67.50; H, 12.20; N, 3.03. Found:
C, 67.30; H, 12.02; N, 2.95.
Dynamic light scattering
0.6
100
1
10.0 mmolL
0.0
0.8
0
100
1
5.0 mmolL
0
100
0.0
0.6
1
Intensity
3.0 mmolL
G()
1
10.0 mmolL
1
5.0 mmolL
1
3.0 mmolL
0
100
0.0
0.3
1
1.5 mmolL
1
1.5 mmolL
0
100
0.0
0.3
1
1.0 mmolL
1
1.0 mmolL
0
0.0
10
-1
10
0
10
1
10
2
/s
10
3
10
4
10
5
10
0
10
1
10
2
10
3
Rh,app /nm
Fig.S1 Time correlation functions for 2-ODTAB at different concentrations (left) and
their corresponding intensity-fraction distributions measured at a detector angle
90o
=
100
60mmolL-1
0
100
30mmolL
Intensity(a.u.)
-1
G( )
60mmolL-1
20mmolL-1
30mmolL-1
0
100
20mmolL-1
0
100
10mmolL-1
10mmolL-1
0
-1
10
0
10
1
10
2
10
s
3
10
10
4
10
5
-1
10
0
10
1
10
10
2
10
3
Rh/nm
Fig.S2 Time correlation functions for 8-8 at different concentrations (left) and their
corresponding intensity-fraction distributions measured at a detector angle
90o
=
10.0 mmolL
0
100
1
2.0 mmolL
1
1.5 mmolL
1
1.0 mmolL
0.5 mmolL
10.0 mmolL
0
100
2.0 mmolL
0
100
1
1.0 mmolL
0
100
1
1
1.5 mmolL
0
100
1
1
5.0 mmolL
Intensity
G( )
5.0 mmolL
100
1
0.5 mmolL
1
1
1
0
10
-1
10
0
10
1
10
2
10
3
10
4
10
5
10
6
s
10
0
10
1
10
2
10
3
10
4
Rh,app/nm
Fig.S3 Time correlation functions for 10-10 at different concentrations (left) and their
corresponding intensity-fraction distributions measured at a detector angle
90o
CONTIN Model (right)
=
1
100
0.5 mmolL
1
0
100
0.2 mmolL
0.1 mmolL
1.0 mmolL
0
100
1
0.2 mmolL
0
100
1
1
0.5 mmolL
Intensity
G( )
1.0 mmolL
0.1 mmolL
1
1
1
0
10
-1
10
0
10
1
10
2
10
3
10
4
10
5
10
6
s
10
0
10
1
10
2
10
3
10
4
Rh,app/nm
Fig.S4 Time correlation functions for 12-12 at different concentrations (left) and their
corresponding intensity-fraction distributions measured at a detector angle
90o
CONTIN Model (right)
=