Supporting Information. for. Advanced Materials, adma Wiley-VCH 2008

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1 Supporting Information for Advanced Materials, adma Wiley-VCH Weinheim, Germany

2 Supporting Information (adma ) Nano-Carbon Superhydrophobic Surface Created from Fullerene Based Hierarchical Supramolecular Assemblies Takashi Nakanishi, 1,2,3 * Tsuyoshi Michinobu, 4 Kaname Yoshida, 5 Naoto Shirahata, 1 Katsuhiko Ariga, 1 Helmuth Möhwald, 2 Dirk G. Kurth 1,2 1 National Institute for Materials Science (NIMS), Sengen, Tsukuba , Japan. 2 Max Planck Institute of Colloids and Interfaces, Potsdam 14424, Germany. 3 PRESTO, Japan Science and Technology Agency (JST), Honcho Kawaguchi, Saitama, Japan. 4 Tokyo University of Agriculture and Technology, Koganei, Tokyo , Japan. 5 Institute for Chemical Research, Kyoto University, Uji, Kyoto , Japan. * To whom correspondence should be addressed. NAKANISHI.Takashi@nims.go.jp Materials and Methods Synthesis (S1) 1: A mixture of 3,4,5-tris(eicosyloxy)benzaldehyde (197 mg, 0.2 mmol), C 60 (142 mg, 0.2 mmol), and N-methylglycine (163 mg, 1.8 mmol) in dry toluene (200 ml) was refluxed for 24 hours. After cooling to room temperature, the reaction mixture was chromatographed on silica gel with toluene then CHCl 3 as eluent. Removal of the solvent in vacuo and the preparative GPC (Bio-beads S-X3, THF) followed by recycle HPLC with CHCl 3, recrystallization from 1,4-dioxane yielded the desired product 1 (121 mg, 0.07 mmol, 35.2 %). 1 H NMR (300 MHz, CDCl 3, 20 C, TMS): 6.97 (br s, 2H), 4.95 (d, 1H, J = 9 Hz), 4.80 (s, 1H), 4.23 (d, 1H, J = 9 Hz), 3.95 (m, 6H), 2.83 (s, 3H), 1.69 (m, 6H), (m, 102H), 0.86 (t, 9H, J = 6 Hz). 13 C NMR (75 MHz, CDCl 3, 20 C, TMS): , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , , 1

3 141.86, , , , , , , , , , , , , 83.66, 77.28, 73.23, 70.01, 69.35, 68.92, 40.10, 31.93, 30.29, 29.74, 29.67, 29.61, 29.44, 29.37, 29.29, 26.10, 26.06, 22.69, IR (KBr, cm 1 ): 2918, 2850, 2774, 1588, 1501, 1466, 1437, 1377, 1357, 1332, 1230, 1177, UV-vis (n-hexane, M): max (, mol 1 dm 3 cm 1 ) = 212 (137600), 255 (98100), 308 (32800). MALDI-TOF-MS (matrix, 2-(4-hydroxyphenylazo)benzoic acid (HABA)): calcd for C 129 H 131 NO ; found [M + ]. Elemental analysis: calcd (%) for C 129 H 131 NO 3 : C 88.87, H 7.57, N 0.80; found C 88.88, H 7.62, N Measurements FT-IR spectra were recorded on a NICOLET NEXUS 670FT-IR spectrometer with a HARRICK temperature control cell TFC M25. A small amount of globular assemblies was placed on a CaF 2 disk plate and the observation was performed under nitrogen atmosphere with various temperature conditions. UV/Vis spectra were recorded on a Shimadzu U 3600 spectrophotometer with temperature controlled cell holder accessory TCC 240A. A small amount of globular assemblies was placed on an inside wall of UV cuvette and the observation was performed under air with various temperature conditions. XRD powder diffraction patterns were measured at 20 C using a RIGAKU RINT Ultima III X-ray diffractometer. Differential scanning calorimetry (DSC) measurements were carried out on a Seiko SII DSC 6220 with a Seiko SII EXSTAR 6000 PC Station. Optical micrographs were taken using an Olympus BX51 microscope equipped with an MP5Mc/OL digital camera. Scanning electron microscopic (SEM) images were obtained using a HITACHI S 4800 scanning electron microscope at an accelerating voltage of 10 kv. Silicon (100) was used as a substrate and a platinum coating was performed using a HITACHI E 1030 Ion Sputter. Cross-section of the multilayer of the globular supramolecular objects of 1 was obtained as follows. Suspension of the globular objects in 1,4-dioxane was deposited on a gold coated quartz plate and dried slowly in air. The modified substrate was cracked to reveal the cross-section of the fabricated film. AFM measurements were carried out using an SII SPA400 with an SPI 4000 Probe Station in dynamic force mode (tapping mode). One drop of a chloroform solution of 1 was spin-coated on a silicon (100) substrate at a spin rate of 1200 rpm, which was subjected to AFM measurements. Supporting Reference 2

4 S1. T. Nakanishi, N. Miyashita, T. Michinobu, Y. Wakayama, T. Tsuruoka, K. Ariga, D. G. Kurth, J. Am. Chem. Soc. 2006, 128,

5 Additional TEM Images Figure S1. a), b) TEM images of supramolecular assemblies of 1 precipitated from 1,4-dioxane solution and c)-e) HR-cryo-TEM images of flake edges of the objects representing the lamellar assemblies. 4

6 Contact Angle Experiments Figure S2. Photographs of a water droplet on the surfaces after exposure to acetone (a, ) and ethanol (b, ) as well as acidic (ph = 2, ), and basic (ph = 12, ) aqueous media, respectively. 5

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