Fullerene multi-nitrogen heterocyclic water-soluble derivatives as well as preparation method and application thereof
A fullerene and water-soluble technology, applied in drug delivery, emulsion delivery, organic chemistry, etc., can solve problems such as large steric hindrance effect, easy cross-interference, short side chains, etc., to improve solubility and enrich Variety effect
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Embodiment 1
[0044] Example 1: C 60 Multiple addition product C with 2-azidoethylamine 60 (NCH 2 CH 2 NH 2 ) x (Compound 1) Preparation
[0045] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under inert gas protection at normal temperature, stir with a magnet, slowly add 2-azidoethylamine solution (5.0mmol of 2-azidoethylamine dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, After the dropwise addition was completed, the temperature was slowly raised to 80° C., and the reaction was heated for 3 days, and the temperature was raised to reflux for 1 day, and the reaction was stopped. During heating, bright purple C 60 The solution gradually turned orange-red and continued to darken to brown. After the reaction liquid was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue was washed with toluene, diethyl ether, and methanol successively to obtain a brownish black solid, namely compound 1, with a yield of 58%.
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Embodiment 2
[0053] Example 2: C 60 Multiple addition product C with 2-azidoacetic acid 60 (NCH 2 COOH) x (Compound 2) and C 60 (NCH 2 COONa) x (Compound 3) Preparation
[0054] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under the protection of inert gas at normal temperature, stir with a magnet, slowly add 2-azidoacetic acid solution (2.0mmol of 2-azidoacetic acid dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, dropwise After completion, the temperature was slowly raised to 50° C., the reaction was heated for 24 hours, and the temperature was continuously raised to reflux for 5 hours. The solvent was removed, and the residue was washed successively with toluene, diethyl ether, and methanol to obtain a tan solid, namely compound 2, with a yield of 95%.
[0055] Weigh 10mg of compound 2 solid powder, dissolve it in an appropriate amount of 1mol / L NaOH, mix well, control the pH value at 12-13, and separate with Sephadex G-15 chromatographic column, neutr...
Embodiment 3
[0058] Example 3: C 60 Multiple addition product C with 3-azidopropionic acid 60 (NCH 2 CH 2 COOH) x (Compound 4) and C 60 (NCH 2 CH 2 COONa) x (Compound 5) Preparation
[0059] Weigh 0.10mmol of C 60 Dissolve in 15ml of chlorobenzene, under the protection of inert gas at normal temperature, stir with a magnet, slowly add 3-azidopropionic acid solution (2.0mmol 3-azidopropionic acid dissolved in 5ml of chlorobenzene) dropwise within 30 minutes, drop After the addition was completed, the temperature was raised slowly to 60° C., and the reaction was heated for 24 hours, and the temperature was continued to rise and reflux for 10 hours. The solvent was removed, and the residue was washed successively with toluene and ethyl acetate to obtain a brownish-yellow solid, namely compound 4, with a yield of 92%.
[0060] The preparation method of Compound 5 was the same as that of Compound 3 in Example 2, except that Compound 2 was replaced by Compound 4 to obtain purified Comp...
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