Supporting Information

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1 Copyright WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 01. Supporting Information for Adv. Mater., DOI:.0/adma.01 Color-Tunable Photoluminescent Fullerene Nanoparticles Jinyoung Jeong, Juyeon Jung, Mijin Choi, Ju Whan Kim, Sang J. Chung, Sujin Lim, Han Lee, and Bong Hyun Chung*

2 Supporting Information Color-tunable photoluminescent fullerene nanoparticles Jinyoung Jeong, Juyeon Jung, Mijin Choi, Ju Whan Kim, Sang J. Chung, Sujin Lim, Han Lee, and Bong Hyun Chung * Materials. C 0 fullerene was purchased from SES Res. (TX, USA). Various oligoethyleneglycols and bases, including lithium hydroxide, were obtained from Sigma-Aldrich (St. Louis, Mo, USA). Characterization. SEM images were obtained from field-emission SEM (FEI, Sirion, The Netherlands) after Pt sputtering. Hydrodynamic diameters were obtained by dynamic light scattering instrument (Otsuka Co., ELS-Z, Japan). The absorption and PL spectra were measured on a UV/Visible spectrophotometer (Beckman Coulter, DU-00, USA) and on a fluorescence spectrophotometer (Perkin-Elmer, LS, UK). The IR spectra were obtained from a FT-IR spectrophotometer (Bruker Optics IF, USA) using a KBr disk. The XPS spectra were measured using an X-ray photoelectron spectroscope (Thermo VG Scientific, UK) with a resolution of 0. ev. 1 The 1 H NMR and 1 C NMR measurements were performed on a Varian Inova 00 MHz NMR spectrometer. The solvent was D O and tetramethylsilane was used as the internal standard. TGA graphs were obtained using a thermogravimetric analyzer (Netzsch, Germany); the samples were run under flowing N gas and at a heating rate of C/min. Element analysis was performed using an element analyzer (Thermo Finnigan, Italy) and the contents were obtained by averaging the values of triple measurements. Bioimaging and cell viability assay. HeLa (human epithelial carcinoma) cells obtained from the American Type Culture Collection (ATCC, Manassas, VA, USA) were cultured according to the process detailed in a previous report. [] For bioimaging, the cells were incubated in media that contained C 0 -TEGs for 0 h. After incubation, the cells were washed three times with PBS. The fluorescence images were obtained using a confocal microscope (Olympus, FV00, USA) with LD0, Ar ion, and HeNeG lasers; the emission filters were 0-, 0-0, and 0-0 nm filters for C 0 -TEGs which prepared with C 0 concentrations at (a) 1

3 , (b) 0., and (c) 1.0 mg/ml in reaction solution, respectively. The cell viability of C 0 - TEGs uptake HeLa cells was assessed using MTT (-(,-dimethylthiazol--yl)-,- diphenyltetrazolium bromide, a tetrazole) (Sigma). HeLa cells ( ) were plated in - well plates (Corning Costar, MA, USA) and incubated with various concentrations of C 0 - TEGs. After h, the cells were treated with MTT according to the manufacturer's protocol. The absorbance values were recorded at approximately nm. The signals were averaged from three values obtained from different wells.

4 Figure S1. Photograph of C 0 -TEGs in various solvents, including a) distilled water (0 mg/ml), b) DMSO ( mg/ml), c) PBS containing 0 mm NaCl ( mg/ml) and d) ethanol (1 mg/ml). Table S1. Dynamic light scattering analysis of the C 0 -TEGs prepared with various C 0 concentrations. All C 0 -TEGs were dissolved in distilled water. C 0 conc. Avg. Size (mg/ml) (nm) ± ± ± ±.

5 Figure S. 1 H NMR spectrum of C 0 -TEG. Figure S. TGA graphs of C 0 -TEG, TEG and C

6 Figure S. The excitation-dependent PL spectra of the C 0 -TEG. Figure S. PL spectra of C 0 -TEG at a) various ph levels and b) in different solvents

7 Table S. Elemental analysis of various C 0 -TEGs prepared with different C 0 concentrations and calculated number of TEG conjugated to one C 0. C 0 conc. (mg/ml) C (%) H (%) O (%) No. TEG If the number of TEG conjugated on C 0 is n, the number of carbon and hydrogen in C 0 -TEG is 0+n and 1n, respectively, according to the molecular formula of TEG (C H 1 O ). And the ratio of the number of carbon atoms to hydrogen atoms are calculated by dividing the weight percentage obtained from the EA by atom weight (1 for carbon and 1 for hydrogen). Combining these features, the number of TEG in each C 0 -TEGs can be obtained by following equation ; C weight (%) from EA/atom weight (1) : H weight (%) from EA/atom weight (1) = (0+n) : 1n

8 Table S. The values of fluorescence quantum yield of various C 0 -TEGs prepared with different C 0 concentrations. C 0 conc. (mg/ml) Φ F The fluorescence quantum yield (Φ F ) was obtained following the protocol in previous literature. [] The standard was quinine sulfate in 0. M H SO (Φ F ~ 0.). The R values were consistent to be 0. in all measurements. 1 1 Figure S. Cell viability assay of different C 0 -TEGs at various concentrations. 1 1