Application of [1,1′:4′,1″]terphenyl-3,3″,5,5″-tetracarboxylic acid_Kain Industrial Additive

Background and overview^[1][2]

[1,1′:4′,1″]terphenyl-3,3″,5,5″-tetracarboxylic acid is an aromatic hydrocarbon derivative that can be used to prepare various organic framework materials.

Apply^[1-2]

1. CN201710240032.2 provides a rare earth organic framework material for detecting vitamin C and a preparation method thereof.

The rare earth organic framework material for detecting vitamin C of the present invention has a long-range ordered crystal structure and regular pores, and its molecular formula is [CeLx(G)(H₂O)] ·(G)n, where L is 1,1′:4′,1″terphenyl-2′,4,4″,5′-tetracarboxylic acid, 1,1′:4′,1terphenyl-3 ,3,5,5″-tetracarboxylic acid, 1,1′:4′,1″terphenyl-2′,3,3,5,5′,5″-hexacarboxylic acid; G represents coordination with rare earth ions The solvent molecules located in the crystal pores are N,N-dimethylformamide, N,N-dimethylacetamide or N,N-diethylformamide; x=1~3; n=1 ~4. The preparation method of the rare earth organic framework material for detecting vitamin C of the present invention includes the following steps: adding the rare earth cerium salt and the organic ligand containing a terphenylcarboxylic acid group into deionized water and an organic solvent, Obtain a mixed solution, then add concentrated HNO₃, put the obtained solution into the inner tank of the reaction kettle, heat and react at 120℃-180℃ for 1-4 days, centrifuge and wash, and obtain a solution for detecting vitamins Rare earth organic framework materials for C.

The specific beneficial effects of the present invention are:

1. The rare earth organic framework material of the present invention can achieve enhanced fluorescence detection of vitamin C. Before adding vitamin C, the fluorescence of the system is very weak. After adding vitamin C, Ce⁴⁺ ions and vitamin C undergo a redox reaction, and the enol in vitamin C is oxidized to form ortho-dione, which will hinder the The photoelectron energy of the ligand in the broken framework is transferred to Ce, thereby enhancing the fluorescence of the ligand itself. This fluorescence-enhanced detection can effectively avoid interference from the system’s own environment and provide a more reliable fluorescence signal. Therefore, the rare earth organic framework material of the present invention can be well applied to the detection of vitamin C.

2. The rare earth organic framework material of the present invention can achieve specific recognition of vitamin C and will not be affected by glycine, leucine, isoleucine, phenylalanine, methionine, glutamine, threonine, Cysteine, glutamic acid, lysine, histidine, glucose, urea, Ca²⁺, I^–, HSO^3- sup>, Na⁺, K⁺, Mg²⁺ and Zn²⁺ and other interferences, This material shows excellent selectivity for the detection of vitamin C.

3. Biological toxicity is an important criterion for evaluating whether a material can be applied in the biomedical field. The rare earth organic framework material of the present invention has low biological toxicity. When co-cultured with cells, even if the concentration of rare earth organic framework materials is high, the cell survival rate is still high, proving that it causes very little damage to biological cells and can be used in the field of biological sciences.

4. The rare earth organic framework material of the present invention can maintain structural stability in water for a long time. After being immersed in water for 7 days, its powder X-ray diffraction pattern still corresponds well to that before immersion, proving its good water stability and ensuring its application in the field of biological sciences.

5. Compared with inorganic rare earth compounds, complexes or organic molecules, the rare earth organic framework material of the present invention is a crystalline material with ordered micropores, a long-range ordered crystal structure and regular pores. A larger ion distance can be obtained through the design of the framework structure and the adjustment of the pore size, so that vitamin C molecules can fully enter the pores and improve the detection efficiency.

6. Compared with other vitamin C detection technologies, the use of the rare earth organic framework material of the present invention can achieve enhanced detection of vitamin C. This method has high sensitivity, small sampling volume, relatively cheaper equipment, and can be easily applied to Direct detection, labeling and identification of biological systems, therefore, the detection of vitamin C is of great significance and prospect.

2. CN201610643864.4 provides a method for synthesizing metal-organic framework materials using p-terphenyl-3,3″,5,5″-tetracarboxylic acid as a ligand and metal terbium, and its application in fluorescence recognition. Applications of dichromate. A terbium-based metal organic framework material. The metal organic framework material uses rare earth metal terbium as the metal center and terphenyltetracarboxylic acid ligands as connectors. The chemical molecular formula is [Tb2(ptptc)1.5(H2O) 4]n, ptptc represents p-terphenyl-3,3″,5,5″-tetracarboxylate, its valence state is negative tetravalent, the structural formula of H4ptptc is as follows:

The metal organic framework material of the present invention is dissolved in pure DMF solution and KX (X=Ac^–, H₂PO_4- , Cl^–, CO₃^2-, Br^–, I^–, SCN-, SO₄^2-, NO^3-) has strong green fluorescence when treated with DMF solution. However, in the DMF solution containing K₂Cr₂O₇, its green fluorescence will be completely quenched. The excitation wavelength of this performance test is 340nm, and the emission peaks are 495, 550, 591 and 623nm respectively. The preparation method of the invention has simple process, is easy to implement, has high yield and is conducive to large-scale preparation.

Main reference materials

[1] CN201710240032.2 Rare earth organic framework materials for detecting vitamin C and preparation method thereof

[2] CN201610643864.4 A terbium-based metal organic framework material, preparation method and application