Supplemental Information
Supporting Information S1:
Grazing-Incidence X-ray Diffraction with Analyzer Crystal
The measured intensity map (upper panel) is corrected with a bending function
2
     tan  B 
(red line) that takes the distortion of the data caused by the analyzer
2
crystal setup into account, yielding the reciprocal space map (lower panel). The appearance of
a single peak at qz = 0 indicates that the fluorocarbon chains for a hexagonal lattice and take
upright orientation. Finally, the integration of the intensity along qz yields the plot presented
in Fig. 2b.
Supplemental Information S2:
Comparison to Yukawa Potential
Effective interactions between nano-domains, compared to Yukawa potential (solid
A
line),  w(r )  exp  r  . Note that the distance r is normalized by the domain size L. As
r
suggested by Fig. 4a, uncorrelated effective interactions that follow Yukawa potential can be
observed only at [FL17] = 5 mol%.
Supporting Information S3:
Synthesis of Fluorinated Lipids
The double chain fluorinated lipid, named FL17 was prepared by the synthetic sequence
outlined below. In the first step, the formation of the fluorinated glycidol was performed in
biphasic conditions (toluene-water) under phase-transfer catalysis. Consequently, the ring
opening reaction took place in solid phase, under microwaves and afforded the corresponding
bicatenar lipid as major product.
1-O-(1H,1H-perfluorooctadecyl) glycidol (F17): A mixture of 1H,1H-perfluoro-1octadecanol (3.7 mmol), 50 % aqueous NaOH (0.84 g, 20.9 mmol, 1.7 mL H2O),
tetrabutylammonium bromide (0.079 g, 0.25 mmol), and benzene (5 mL) was stirred at room
temperature for 15 min. Epichlorhydrin (2 mL, 26 mmol) was then added and the reaction
mixture heated to 75 °C for 18 h. The reaction mixture was than cooled to 0°C, filtered and
washed with water. The white solid was then dried over night. Yield 70%. 1H-NMR (CDCl3):
2.56 (dd, 1H, CH2 epoxide, J=4.6, 2.7 Hz); 2.75 (t, 1H, CH2 epoxide, J=4.6 Hz); 3.10 (m, 1H,
CH epoxide); 3.46 (dd, 1H, CH2-O, J=11.8, 5.9 Hz); 3.90 (dd, 1H, CH2-O, J=11.8, 2.5 Hz);
3.99 (t, 2H, CH2-CF2, J=13.5); 13C-NMR (CDCl3): 44.04 (CH2 epoxide); 50.83 (CH epoxide);
68.52 (t, CH2-CF2, 2J(C,F)=26 Hz); 73.48 (CH2-O); 19F-NMR (CDCl3): -81.30 (t,
3
J(F,F)=13.05, CF3), -119.97 (CF2-CH2), -122.26, -123.21, -123.50 (all the others CF2), 126.64 (CF2-CF3). EI: m/z=956 [MH]+; m/z=913 (C17F35CH2OCH2+). Elemental analysis:
C21H7F35O2, th. %C: 26.38, %H: 0.74, exp. %C: 25.18, %H: 0.98.
1,3-bis-O-(1H, 1H-perfluorooctadecyl) glycerol (FL17): A mixture of 1-O-(1H,1Hperfluorooctadecyl) glycidol (F17) (1g, 1.6 mmol), 1H,1H-perfluorooctadecanol (0.91 g,
3.5 mmol) and potassium methoxide (40 mg, 0.54 mmol) was heated to 100 °C under N2 and
microwaves (P=300 W) for 2 h. The reaction mixture was than cooled to room temperature
and added in 100 mL THF. The mixture was maintained under stirring for 2h, then the
solution was filtered and the solvent evaporated. The product was purified by several
recristalisations in CH2Cl2. Yield 36%. 1H-NMR (CDCl3/Freon F-113): 3.70-3.87 (d, 4H,
CH2-CH-OH, J=4.9 Hz); 3.96-4.14 (2t, 4H, CH2-CF2, J=13.5 and 1H, CH-OH); 13C-NMR
(CDCl3/Freon F-113): 67.95 (t, CH2-CF2, 2J(C,F)=26.5 Hz); 72.63 (CH-CH2-O); 76.62 (CHOH). Elemental analysis: C39H10F70O3, th. %C: 25.23, %H: 0.54, exp. %C: 23.48, %H: 1.17.
[1]
W. Huang, C. Jin, D. K. Derzon, T. A. Huber, J. A. Last, P. P. Provencio, A. S.
Gopalan, M. Dugger, D. Y. Sasaki, J. Colloid Interf. Sci. 2004, 272, 457.