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CN-121974857-A - Preparation method of gold complex containing benzimidazole structure and nano particles thereof

CN121974857ACN 121974857 ACN121974857 ACN 121974857ACN-121974857-A

Abstract

The invention belongs to the technical field of organic synthesis and nano material preparation, and particularly relates to a gold complex containing a benzimidazole structure and a preparation method of nano particles thereof. Adding the gold complex containing the benzimidazole structure and alkali into water, mixing, and adding NaBH 4 for reaction to obtain the gold-carbene nanoparticle. The preparation method of the gold complex containing the benzimidazole structure and the nano particles thereof has the advantages of simple process, mild reaction condition and higher yield, so as to obtain the compound and the nano material with excellent performance and potential application value.

Inventors

  • TANG BO
  • LI LU
  • Tan Shuzhi
  • SI HAIBIN

Assignees

  • 山东师范大学

Dates

Publication Date
20260505
Application Date
20260129

Claims (10)

  1. 1. A gold complex containing a benzimidazole structure, characterized in that the structural formula of the gold complex containing a benzimidazole structure is as follows: compound 5.
  2. 2. A process for preparing a benzimidazole structure-containing gold complex according to claim 1, wherein the compound 5 is represented by the formula 4 Carrying out ligand exchange reaction with Au (SMe 2 ) Cl under alkaline condition; The mol ratio of the compound 4 to Au (SMe 2 ) Cl to the alkali is (10-12): 1 (30-35); The temperature of the ligand exchange reaction is 55-65 ℃, and the time of the ligand exchange reaction is 10-15h.
  3. 3. The method for preparing a benzimidazole structure-containing gold complex according to claim 2, wherein the compound 4 is represented by the compound 3 Carrying out ring opening reaction with 1, 4-butane sultone to obtain the product; The molar ratio of the compound 3 to the 1, 4-butane sultone is 1 (1.2-1.8); the temperature of the ring-opening reaction is 105-115 ℃, and the time of the ring-opening reaction is 20-30 h.
  4. 4. The method for preparing a benzimidazole structure-containing gold complex according to claim 3, wherein the compound 3 is represented by the compound 2 Carrying out substitution reaction with 2-bromopropane under alkaline condition; the mass ratio of the compound 2, 2-bromopropane to the alkali is (5-6): (7-10): (7-15); the temperature of the substitution reaction is 45-55 ℃, and the time of the substitution reaction is 1-3 h.
  5. 5. The method for preparing a gold complex containing a benzimidazole structure according to claim 4, wherein the compound 2 is prepared by esterification of 5-benzimidazole carboxylic acid and ethanol under concentrated sulfuric acid; The ratio of the 5-benzimidazole carboxylic acid to the ethanol to the concentrated sulfuric acid is 5g to 120mL (4.2-8) mL; the temperature of the esterification reaction is 60-85 ℃, and the time of the esterification reaction is 10-15 h.
  6. 6. Use of a gold complex containing a benzimidazole structure according to claim 1 for the preparation of gold-carbene nanoparticles.
  7. 7. The preparation method of the gold-carbene nanoparticle is characterized by comprising the following steps of: The benzimidazole structure-containing gold complex according to claim 1, wherein the compound 6 is obtained by hydrolysis under alkaline conditions ; And adding the compound 6 and alkali into water, mixing, and adding NaBH 4 for reaction to obtain the gold-carbene nanoparticle.
  8. 8. The method for preparing gold-carbene nanoparticle according to claim 7, wherein, The molar ratio of the gold complex containing the benzimidazole structure to the alkali is 1 (6-7); the temperature of the hydrolysis reaction is 85-95 ℃, and the time of the hydrolysis reaction is 1-5h; The mass ratio of the compound 6 to the alkali to the NaBH 4 is (60-100): 10-50, and the ratio of the alkali to the water is 0.2-2.5g/L.
  9. 9. A gold-carbene nanoparticle prepared by the method for preparing a gold-carbene nanoparticle according to claim 7 or 8.
  10. 10. Use of the gold-carbene nanoparticle of claim 9 in catalysis, biosensors, biomedical and chiral materials.

Description

Preparation method of gold complex containing benzimidazole structure and nano particles thereof Technical Field The invention belongs to the technical field of organic synthesis and nano material preparation, and particularly relates to a gold complex containing a benzimidazole structure and a preparation method of nano particles thereof. Background Gold nanoparticles (AuNPs) show wide application prospects in the fields of catalysis, biomedicine, sensing, functional materials and the like by virtue of unique physicochemical properties such as remarkable local surface plasmon resonance effect, high specific surface area, good biocompatibility, and easy regulation and control of size and morphology. However, the high surface energy of AuNPs makes the AuNPs in a thermodynamically unstable state, aggregation/aggregation is easy to occur, the stability of the AuNPs is greatly influenced by environmental factors such as pH, salt concentration, temperature and the like, and meanwhile, the coupling efficiency, molecular orientation and density of the existing AuNPs surface modification are difficult to accurately control, so that batch-to-batch differences are caused, and the consistency and reliability of the product performance are seriously influenced. The gold complex constructed by benzimidazole ligand and the corresponding gold nano material thereof have potential application value in anti-cancer drug development, heterogeneous catalysis and advanced material preparation due to the special electronic structure and coordination capability. However, the existing synthesis method still has various limitations, such as complicated reaction steps, low product yield, use of harmful reagents or solvents, high energy consumption, poor environmental compatibility and the like, and restricts the large-scale preparation and practical application of the materials. Disclosure of Invention The invention aims to provide a preparation method of a gold complex containing a benzimidazole structure and nano particles thereof, which has the advantages of simple preparation process, mild reaction conditions and higher yield, so as to obtain a compound and a nano material with excellent performance and potential application value. In order to achieve the above purpose, the technical scheme of the invention is as follows: in a first aspect, the present invention provides a gold complex comprising a benzimidazole structure, the gold complex comprising a benzimidazole structure having the structural formula: compound 5. The gold complex has an asymmetric, multifunctional design and is formed by a gold atom and a ligand through a coordination bond, wherein the ligand can provide an N-heterocyclic carbene ligand coordinated with gold. The structure integrates isopropyl (steric hindrance), sulfonate (water solubility) and ester group (can be further functionalized), and the nano particles prepared from the gold complex containing the benzimidazole structure have potential application value in the fields of catalysis, biosensing, drug delivery and the like, and provide new material basis and technical support for research and development in related fields. In a second aspect, the present invention provides a method for preparing a gold complex containing a benzimidazole structure according to the first aspect, wherein the compound 5 is represented by the compound 4Carrying out ligand exchange reaction with Au (SMe 2) Cl under alkaline condition; The mol ratio of the compound 4 to Au (SMe 2) Cl to the alkali is (10-12): 1 (30-35); The temperature of the ligand exchange reaction is 55-65 ℃, and the time of the ligand exchange reaction is 10-15h. Specifically, the molar ratio of the compound 4, au (SMe 2) Cl to the base is 10:1:30, 12:1:35, 11:1:32; The temperature of the ligand exchange reaction is 55, 60 or 65 ℃, and the time of the ligand exchange reaction is 10, 12, 14 or 15 hours. More specifically, the molar ratio of the compound 4 to Au (SMe 2) Cl to the base is 5.02:0.45:15.06, the base is K 2CO3, and the solvent is acetone. The temperature of the ligand exchange reaction is 60 ℃, and the time of the ligand exchange reaction is 12 h. After the ligand exchange reaction is finished, the method further comprises filtering, vacuum solvent removal and silica gel column chromatography, wherein the number of silica gel adopted by the silica gel column chromatography is 300-400 meshes, the mobile phase is dichloromethane-methanol, and the volume ratio of the dichloromethane-methanol is (95-5) to (5-1). Specifically, the volume ratio of dichloromethane-methanol is 95:5. In this ligand exchange process, the choice of Au (SMe 2) Cl over other gold sources (e.g., HAuCl 4) is critical to success. It avoids the risk of gold (I) being reduced to gold (0) (nanoparticles), ensuring the formation of molecular complexes. The K 2CO3 is used instead of stronger alkali (such as NaH), so that the conditions are milder, the operation is safer, and the me