A highly selective AIE fluorogen for lipid droplet imaging in live cells and green algae

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1 Electronic Supporting Information highly selective IE fluorogen for lipid droplet imaging in live cells and green algae Erjing Wang, ab Engui Zhao, ab Yuning Hong, ab Jacky W. Y. Lam, ab and en Zhong Tang* abc a HKUST-Shenzhen Research Institute, No. 9 Yuexing 1st RD, South rea, Hi-tech Park, Nanshan, Shenzhen, 51857, China. tangbenz@ust.hk Tel: , Fax: b Department of Chemistry, Division of iomedical Engineering, Institute for dvanced Study and Institute of Molecular Functional Materials, The Hong Kong University of Science & Technology, Clear Water ay, Kowloon, Hong Kong, China c Guangdong Innovative Research Team, SCUT-HKUST Joint Research Laboratory, State Key Laboratory of Luminescent Materials and Device, South China University of Technology, Guangzhou, 5164, China Contents Fig. S1 bsorption spectra of TPE-mr and TPE-ml in pure THF solutions. Fig. S2 () bsorption and () emission spectra of TPE-ml in different solvents. Fig. S3 Cytotoxicity of TPE-ml at different concentrations on HeLa and liver LO2 cells determined by MTT assay. Fig. S4 Fluorescent images of HeLa cells stained with () 2, () 1, (C) 2 and (D) 5 μm TPE-ml for 15 min. Fig. S5 () Emission spectra of TPE-ml (1 μm) in dichloromethane/n-hexane with different n-hexane fractions. () Plot of the peak wavelength versus the hexane fraction. Fig. S6 Confocal images of oleic acid (5 μm)-treated HeLa cells stained with TPE-ml (1 μm ) for 15 min. Fig. S7 Signal loss (%) of fluorescence intensity of Nile red in oleic acid-treated HeLa cells with scanning time. Staining time: 5min; scanning speed: s/scan; excitation wavelength: 488 nm. Fig. S8 Particle size analysis of TPE-ml (1 μm) nanoaggregates formed in MEM at 25 o C. S1

2 Fig. S9 () right-field and () fluorescent images of liver LO2 cells stained with TPE-ml (1 μm) in a large view after incubation in the presence of 5 μm oleic acid for 6 h. Staining time: 15 min; excitation wavelength: nm. Fig. S1 Fluorescent images of () HeLa and () liver LO2 cells stained with 1 μm TPE-ml for 15 min. Excitation wavelength: nm; scale bar: 2 μm. Fig. S11 Fluorescent images of liver LO2 cells stained with () Nile red (.314 μm ) for 5 min and () TPE-ml (1 μm) for 15 min after incubation in the presence of oleic acid (5 μm) for 6 h. (C) Merged image of panels () and (). Excitation wavelength: nm for Nile red and nm for TPE-ml. Fig. S12 Fluorescent images of liver LO2 cells stained with Nile Red (1 ng/ml,.314 μm) after incubation in the presence of (), () 12.5, (C) 25 and (D) 5 μm oleic acid for 6 h. Staining time: 5 min; excitation wavelength: nm. 3x1 4 TPE-ml TPE-mr Molar absorptivity ( M -1 cm -1 ) 2x1 4 1x Fig. S1 bsorption spectra of TPE-mr and TPE-ml in pure THF solutions. Concentration: 1 M. S2

3 Normalized absorption hexane toluene THF E acetone DMF DMSO Normalized PL hexane toluene THF E acetone DMF DMSO Fig. S2 () bsorption and () emission spectra of TPE-ml in different solvents. Excitation wavelength: 45 nm HeLa cell LO2 cell 1 Cell viability (%) Concentration ( M) Fig. S3 Cytotoxicity of TPE-ml at different concentrations on HeLa and liver LO2 cells determined by MTT assay. S3

4 Fig. S4 Fluorescent images of HeLa cells stained with () 2, () 1, (C) 2 and (D) 5 μm TPE-ml for 15 min. Excitation wavelength: nm. PL intensity (au) f hex (vol%) Peak wavelength (nm) Hexane fraction (vol%) Fig. S5 () Emission spectra of TPE-ml (1 μm) in dichloromethane/n-hexane with different n-hexane fractions. () Plot of the peak wavelength versus the hexane fraction. Fig. S6 Confocal images of oleic acid (5 μm)-treated HeLa cells stained with TPE-ml (1 μm ) for 15 min. () Phase contrast, () upon excited at 45 nm, and (C) merged image of panels and. S4

5 1 Emission intensity (au) Scanning time (min) Fig. S7 Signal loss (%) of fluorescence intensity of Nile red in oleic acid-treated HeLa cells with scanning time. Staining time: 5min; scanning speed: s/scan; excitation wavelength: 488 nm. 1 8 Intensity (au) 6 4 D m = 178 nm Particle size (nm) Fig. S8 Particle size analysis of TPE-ml (1 μm) nanoaggregates formed in MEM at 25 o C. S5

6 .5 mm Fig. S9 () right-field and () fluorescent images of liver LO2 cells stained with TPE-ml (1 μm) in a large view after incubation in the presence of 5 μm oleic acid for 6 h. Staining time: 15 min; excitation wavelength: nm. Fig. S1 Fluorescent images of () HeLa and () liver LO2 cells stained with 1 μm TPE-ml for 15 min. Excitation wavelength: nm; scale bar: 2 μm. S6

7 C 2 m Fig. S11 Fluorescent images of liver LO2 cells stained with () Nile red (.314 μm ) for 5 min and () TPE-ml (1 μm) for 15 min after incubation in the presence of oleic acid (5 μm) for 6 h. (C) Merged image of panels () and (). Excitation wavelength: nm for Nile red and nm for TPE-ml. C D 2 m Fig. S12 Fluorescent images of liver LO2 cells stained with Nile Red (1 ng/ml,.314 μm) after incubation in the presence of (), () 12.5, (C) 25 and (D) 5 μm oleic acid for 6 h. Staining time: 5 min; excitation wavelength: nm. S7