CN-122010907-A - Fe based on phenanthroimidazole3+Specific recognition fluorescent probe and application thereof

CN122010907ACN 122010907 ACN122010907 ACN 122010907ACN-122010907-A

Abstract

The invention discloses a Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole and application thereof, wherein the fluorescent probe takes phenanthroimidazole groups as electron donor units and benzene rings substituted by benzene rings and fluorine atoms as electron acceptor units. By respectively introducing imidazole groups and fluorine atoms in the directions of the short axis and the long axis of the molecule, the fine regulation and control of the excited state property is realized, and the vibration coupling in the first single excited state is effectively inhibited, so that the blue light emission with high purity is obtained, and the photophysical property of the material is obviously improved. The fluorescent material has the advantages of simple synthesis method, easy purification, excellent thermal stability and remarkable signal response, and has wide application prospect in detection of Fe 3+ in high-temperature industrial environment.

Inventors

ZHU SHENGBO
CHI XIAOYAN
NIU XIAOLING

Assignees

西安工业大学

Dates

Publication Date: 20260512
Application Date: 20260205

Claims (3)

1. Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole, which is characterized by having the following structural formula: Wherein Ar represents 、、、、、 Any one of them.
2. The phenanthroimidazole-based Fe 3+ -specific recognition fluorescent probe as set forth in claim 1, wherein Ar represents 、、、 Any one of them.
3. Use of the fluorescent probe of claim 1 for detecting Fe 3+ in a high temperature complex industrial environment.

Description

Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole and application thereof Technical Field The invention belongs to the technical field of organic luminescent materials, and particularly relates to a Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole and application thereof. Background Fe 3+ is used as an important transition metal ion and has a key effect in the processes of industrial catalysis, environmental monitoring, biological metabolism and the like. The existing Fe 3+ identification material faces serious technical bottlenecks in complex industrial environments such as high temperature, strong corrosion, high interference and the like. The existing probe focuses on a single recognition function, lacks a multifunctional integrated design with structural stability, high selectivity and reversible detection at high temperature, and has excellent thermal stability in a natural rigid structure of a Phenanthroimidazole (PI) skeleton, and the thermal stability requirement of a material in a high-temperature environment is just matched. Meanwhile, the conjugated structure of the imidazole ring N atom and the phenanthrene ring of PI can be used for replacing and regulating the front line orbit energy level through the D-PI-A configuration, so that bipolar carrier transmission capability is provided for the material, charge injection and transmission in the sensing device are balanced, and signal stability is improved. Odedara et al (ChemPhotoChem, 2024, 8, e 20240018) disclose the synthesis and use of 3 phenylnaphthylimidazole-based derivatives, wherein Pq-pF-OH is optimally performed, the decomposition temperature T d =348 ℃ meets preset requirements, however, the mass residual R W is 5% less than the standard, so that the long-term stability in a high-temperature environment cannot meet the practical application requirements. Disclosure of Invention The invention aims to provide a Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole, which adopts phenanthroimidazole groups with rigid structures to improve the thermal stability of molecules, introduces benzene rings and fluorine-containing benzene rings as electron-withdrawing groups, adjusts the excitation state property, and adjusts the defects of poor signal and low thermal stability of the fluorescent probe in high-temperature complex environments. The invention provides a Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole, which has the structural formula as follows: Wherein Ar represents 、、、、、Any one of them. Further, ar preferably represents、、、Any one of them. The method for synthesizing the Fe 3+ specific recognition fluorescent probe based on phenanthroimidazole comprises the following steps: The preparation method comprises the steps of 1, adding phenanthrenequinone, 1- (4-aminophenyl) imidazole, p-bromobenzaldehyde and ammonium acetate into acetic acid according to a molar ratio of 1:1-1.5:1-1.3:4-6, reacting for 1-3 hours at 110-120 ℃ in a nitrogen atmosphere, pouring the reaction solution into saturated saline after the reaction is finished, and obtaining a compound MZPIBr through filtration, ethanol washing and N, N-dimethylformamide recrystallization. The reaction equation is as follows: MZPIBr Step 2, adding MZPIBr, phenylboronic acid compound, tetrabutylammonium bromide and dichlorodi-tert-butyl- (4-dimethylaminophenyl) palladium (II) into DMF according to a molar ratio of 1:1.3-2:2-2.5:0.05-0.1, then adding K 2CO3 aqueous solution, wherein the molar ratio of K 2CO3 to MZPIBr is 5-7:1, reacting for 6-10 hours at 70-80 ℃ in nitrogen atmosphere, after the reaction is finished, pouring the reaction solution into saturated saline, filtering, washing with ethanol, and performing column chromatography to obtain a fluorescent probe, wherein the reaction equation is as follows: MZPIBr The invention also provides application of the fluorescent probe in detecting Fe 3+ in a high-temperature complex industrial environment. The beneficial effects of the invention are as follows: According to the fluorescent probe, the phenanthroimidazole group is used as an electron donor unit, the benzene ring substituted by the benzene ring and the fluorine atom is used as an electron acceptor unit, the imidazole group and the fluorine atom substituent are introduced in the directions of the minor axis and the major axis of the molecule, and the excitation state property of the fluorescent probe is reasonably controlled by changing the quantity of the fluorine atoms to adjust the electron withdrawing capability, so that vibration coupling in a first single excitation state is inhibited, high-purity blue light emission is obtained, further, the obvious signal response of a complex environment is realized, and meanwhile, the fluorescent molecule has excellent thermal stability. The preparation method of the fluorescent probe is simple, easy to purify, high in luminous efficiency