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4 protocols using am 250 spectrometer

1

Synthesis of Fluorescent Lactose Derivatives

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All reagents were obtained from commercial sources. D-lactose, acetic anhydride, N,N-dimethylformamide (DMF), trichloroacetonitrile, 1,8-diazabicyclo [5.4.0]undec-7-ene (DBU), boron trifluoride diethyl etherate (BF3·Et2O), propargyl alcohol, sodium metal, Dowex-50 resin (H+ form), 5-bromovaleryl chloride, 2,4-dimethyl pyrrole, triethylamine (TEA), N-iodosuccimide (NIS) were purchased from Sigma Aldrich (St. Louis, MO, USA). Sodium azide, sodium ascorbate, copper (II) sulfate pentahydrate, sodium hydroxide (NaOH), sulfuric acid (H2SO4), sodium hydrogen carbonate (NaHCO3), magnesium sulfate (MgSO4), and ammonium carbonate [(NH4)2CO3] were procured from Daejung Chemical (Gyeonggi-do, South Korea) and used without further purification. Ethyl acetate (EtOAc), dichloromethane (CH2Cl2), tetrahydrofuran (THF), methanol, and other solvents were of analytical grade and were dried under calcium hydride prior to use, except THF.
All compounds were characterized by 1H- and 13C-NMR spectroscopy on a Bruker AM 250 spectrometer (Billerica, MA, USA) and high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) on a SYNAPT G2-Si high definition mass spectrometer (Waters, London, United Kingdom).
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2

Characterization of Chemical Compounds

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All the chemicals were obtained commercially and utilized without purification. Methanol, ethanol, and DMSO-d6 were procured from Sigma Aldrich, purified, and dried by standard analytical procedures. The melting points were determined using Gallon Kamp’s melting point instrument. The 1H NMR (300 MHz) and 13C NMR (75.43 MHz) spectra were collected on a Bruker AM-250 spectrometer utilizing CDCl3 and DMSO as internal standards. A UV-Visible spectrophotometer was used to obtain UV-Visible absorption spectra, model UV-1700. Elements were analyzed using a Leco CHNS-932 Elemental Analyzer (Leco Corporation, USA).
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3

Synthesis and Characterization of BODIPY Nanoparticles

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Almost all reagents and chemicals were obtained from Sigma Aldrich (St. Louis, MO, USA). Some solvents such as dichloromethane (CH2Cl2), methanol (MeOH), or MgSO4, sodium azide (NaN3), sodium ascorbate (NaAsc), Copper (II) sulfate pentahydrate (CuSO4.5H2O) were purchased from Daejung chemical (Gyeonggi-do, South Korea), and used without further purification. Lactose-propargyl was synthesized in our previous literature24 .
All compounds were characterized by 1H and 13C-NMR spectroscopy on a Bruker AM 250 spectrometer (Billerica, MA, USA). The impurity of the products was checked by thin-layer chromatography (TLC, silica gel 60 mesh). UV spectra were measured on a Shimadzu UV-1650PC spectrometer, and Fluorescence spectra were carried on a Hitachi F-7000 spectrometer. The size and morphology of BODIPY NPs were analyzed by using dynamic light scattering (DLS) on Malvern Zetasizer Nano ZS90 and transmission electron microscopy (TEM). We used machine JEOL- JEM 2100F at an accelerating voltage of 200 kV. The sample for TEM was prepared according to our reported literature51 .
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4

Characterization of Silica Nanoparticles

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Absorption measurements were carried out on a Shimadzu UV-1650 PC spectrometer (Kyoto, Japan) in 1 cm quartz cuvette from 200 to 900 nm. Fluorescence spectra were obtained using a Hitachi F-7000 spectrometer (Tokyo, Japan). Solutions of a concentration of 10 µM were used for both absorption and fluorescence measurements at room temperature (∼25 °C). Absolute quantum yield measurements were carried out using an absolute photoluminescence (PL) quantum yield measurement system (C11347, Hamamatsu Photonics, Hamamatsu, Japan) equipped with a 150-W xenon lamp (Hamamatsu Photonics, Hamamatsu, Japan). All compounds were characterized by 1H-NMR spectroscopy on a Bruker AM 250 spectrometer (Billerica, MA, USA). The purity of the products was checked by thin-layer chromatography (TLC, silica gel 60 mesh). The silica nanoparticles were detached by Eppendorf Centrifuge Model 5804. The size and morphology of silica nanoparticles were analyzed by using transmission electron microscopy (TEM) (JEOL, MA, USA). We used machine JEOL-JEM 2100F (Peabody, MA, USA) at an accelerating voltage of 200 kV. To prepare TEM samples, 0.001 wt.% solutions of silica nanoparticles were dropping onto holey carbon film copper. The solvent then was evaporated at room temperature.
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