Use of non-periphery substituted phthalocyaniu metal complex
A metal complex and non-peripheral technology, which is applied in the field of non-peripheral substituted phthalocyanine metal complexes, can solve problems such as difficult aggregation, and achieve the effects of difficult aggregation, improved photodynamic activity, and increased fluorescence quantum yield
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[0041] The steps of the preparation method of the non-peripheral substituted phthalocyanine metal complex of structural formula (1) are:
[0042] (1): With 3-nitrophthalonitrile and the alcohol derivative of the substituting group described in claim 1 as the reactant, the molar ratio of the two is 1: 0.8-1.2; the alcohol derivative is butylparaben, 4-hydroxybenzoic acid, 3-(4-hydroxyphenyl)propionic acid, 3-hydroxybenzoic acid, methyl salicylate, ethyl N-acetyltyrosine, or N-acetyl One of the base tyrosine;
[0043] (2): With dimethyl sulfoxide or N, N-dimethylformamide as solvent, the amount of solvent needs 3-8ml for every mmol reactant 3-nitrophthalonitrile, in the presence of potassium carbonate and nitrogen Under the protection of , react for 8-24 hours under room temperature-60 waste, obtain intermediate substituted phthalonitrile, described substituted phthalonitrile is as shown in formula (7), R and claim 1 described substituting group R same;
[0044] (3): Using th...
Embodiment 1
[0077] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-butoxycarbonylphenoxy)phthalocyanine zinc(II)
[0078] This compound can also be called four-a-(4-butoxycarbonylphenoxy)zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:
[0079]
[0080] (1) Preparation of intermediate 3-(4-butoxycarbonylphenoxy) phthalonitrile:
[0081] Under the protection of nitrogen, 5mmol butylparaben and 4-6mmol (preferably 5mmol) 3-nitrophthalonitrile were added to 15-40ml (preferably 20ml) dimethyl sulfoxide (DMSO) or N, N - In dimethylformamide (DMF), after stirring at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, and react for 12 to 24 hours (preferably 16 hours). The reaction mixture was added to 200ml of ice-water mixture, stirred to precipitate a large amount of white precipitate, left to stand, filtered by suction, washed with water until neutral, the filter cake was collected, dried under normal pressure at 70°C to obt...
Embodiment 2
[0088] Synthesis of 1,8(11), 15(18), 22(25)-tetrakis(4-carboxyphenoxy)phthalocyanine zinc(II)
[0089] This compound can also be called four-a-(4-carboxyphenoxy) zinc phthalocyanine (II), and its structure is shown in formula 1, wherein:
[0090]
[0091] (1) Preparation of intermediate 3-(4-carboxyphenoxy) phthalonitrile:
[0092] Under the protection of nitrogen, 0.69g (5mmol) 4-hydroxybenzoic acid, 0.87g (5mmol) 3-nitrophthalonitrile were dissolved in 20ml dimethyl sulfoxide (DMSO), after stirring at room temperature for 10 minutes, add 1.5 g (10.9 mmol) of anhydrous potassium carbonate, after 10 minutes, add 1.0 g of potassium carbonate, and continue the reaction for 12 to 24 hours (preferably 14 hours). Suction filter the reaction mixture, collect the filtrate, add 200ml ice-water mixture to the filtrate, adjust the pH value to 1~3 (preferably 2) with 2mol / L HCl solution, the product is precipitated out, filter, wash with water until neutral, collect The filter cake ...
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