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3 protocols using potassium carbonate

1

Synthesis of Heterocyclic Compounds

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n-Butyllithium, phosphinic
acid, potassium carbonate, pyridine, o-phenylendiamine, o-dichlorobenzene, cuprous iodide, trifluoroacetic anhydride,
18-crown-6, carbazole, phenothiazine, diisopropylethylamine, sodium t-butoxide, and tribenzylidene acetone dipalladium (II)
were purchased from Energy Chemical. Tetrahydrofuran, dichloromethane,
petroleum ether, methanol, and ethyl acetate were purchased from Sinopharm
Chemical Reagent Co., Ltd. Chemicals were used without further purification
unless otherwise noted. Anhydrous solvents were distilled from commercial
sources with sodium/benzopheneone or calcium hydride.
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2

Synthesis of Polycyclic Aromatic Compounds

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Benzene-1,3,5-triyltriboronic acid pinacol ester and tris(4-boronic acid pinacol ester phenyl)amine were purchased from Sukailu, Suzhou, China. 2,7-dibromopyrene, chlorothalonil, nitrofen, trifluralin, and dicloran were all purchased from Aladdin, Shanghai, China. Potassium carbonate was obtained from Energy Chemical, Shanghai, China. Tetrakis(triphenylphosphine)palladium was obtained from Sigma-Aldrich, St. Louis, MO, USA. Other chemicals and solvents were purchased from commercial suppliers and used without further purification. All reactions were performed under a purified nitrogen atmosphere.
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3

Synthesis and Characterization of Photosensitizers

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Human serum albumin (HSA, ≥ 98%), Bovine serum albumin (BSA, ≥ 98%), β-Lactoglobulin from bovine blood (β-LG, ≥ 90%), L-Cysteine (Cys, ≥ 98%), IR-780 ( ≥ 98%), and anhydrous dimethyl sulfoxide (DMSO, ≥ 99%) were purchased from Sigma-Aldrich. ICG (modified) for human injection was purchased from Dandong Yichuang Pharmaceutical Co. Ltd. IR-808 ( ≥ 95%) was purchased from Beijing Zhongying Biotechnology Co., Ltd. Cyanine5 NHS ester (Cy5, ≥ 99%) was purchased from Aladdin (Shanghai, China). Recombinant human albumin domain I (DI, ≥ 95%), recombinant human albumin domain II (DII, ≥ 95%), and recombinant human albumin domain III (DIII, ≥ 95%) were purchased from Albumin Therapeutics LLC. Benzo[cd]indol-2(1H)-one, phosphorus pentasulfide, pyridine, sodium hydroxide (NaOH), methyl iodide, acetone, methanol, 2,2-dimethyl-1,3-dioxane-4,6-dione, ethanol, triethylamine, ethyl iodide, N,N-Dimethylformamide (DMF), potassium carbonate, concentrated hydrochloric acid (HCl), potassium iodide, acetic acid, acetic anhydride, 1-iodopropane, 1,4-butylenesulfone, potassium hydroxide, N-methylpyrrolidone(NMP), 2,6-di-tert-butyl-4-methyl pyridine (DTBMP), toluene, 1-butanol, and ethyl 6-bromohexanoate were purchased from Energy Chemical.
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