CN-122010838-A - Naphthalimide fluorescent dye and preparation method and application thereof

CN122010838ACN 122010838 ACN122010838 ACN 122010838ACN-122010838-A

Abstract

The invention discloses a naphthalimide fluorescent dye, a preparation method and application thereof, relating to the technical field of fluorescent dye, the invention takes naphthalimide compound as a two-photon fluorescent substrate, leading in palladium ion recognition groups through chemical reaction, so that fluorescence of the compound is quenched to obtain naphthalimide fluorescent dye; the naphthalimide fluorescent dye can generate a specific reaction after recognizing palladium ions, so that fluorescence is enhanced, and 460 nm-wavelength fluorescence emission is generated in a 360 nm-wavelength excited state.

Inventors

DOU YANDONG
SHEN HONGGE
SUO FENG

Assignees

安徽峆一药业股份有限公司

Dates

Publication Date: 20260512
Application Date: 20251229

Claims (10)

1. A naphthalimide fluorescent dye has the following structural formula: 。
2. the method for preparing naphthalimide fluorescent dye according to claim 1, comprising the steps of: S1, 4-bromo-1, 8-naphthalene dicarboxylic anhydride and n-butylamine undergo an acylation reaction to obtain an intermediate 1; s2, performing carbonylation reaction on the intermediate 1 and N, N-dimethylformamide to obtain an intermediate 2; S3, performing oxidation-reduction reaction on the intermediate 2 and hydroxylamine hydrochloride to obtain an intermediate 3; S4, carrying out substitution reaction on the intermediate 3 and 3-bromopropyne to obtain the naphthalimide fluorescent dye; The synthetic route is as follows: 。
3. The method for preparing naphthalimide fluorescent dye according to claim 2, wherein the molar ratio of 4-bromo-1, 8-naphthalic anhydride to n-butylamine is 1 (1-2).
4. A process for producing a naphthalimide fluorescent dye as claimed in claim 2, wherein the carbonylation reaction is carried out in the presence of a metal catalyst.
5. The method for preparing a naphthalimide fluorescent dye as claimed in claim 4, wherein the metal catalyst is manganese dioxide and samarium.
6. The method for preparing a naphthalimide fluorescent dye according to claim 2, wherein the molar ratio of the intermediate 2 to hydroxylamine hydrochloride is 1 (1-4).
7. The method for producing a naphthalimide fluorescent dye as claimed in claim 2, wherein the redox reaction is performed under alkaline conditions provided by at least one of sodium acetate, potassium carbonate, sodium carbonate, and sodium bicarbonate.
8. The method for preparing naphthalimide fluorescent dye according to claim 2, wherein the molar ratio of the intermediate 3 to 3-bromopropylene is 1 (1-2).
9. The method for preparing a naphthalimide fluorescent dye according to claim 2, wherein the substitution reaction is performed in the presence of an acid-binding agent, preferably at least one of sodium hydride and potassium hydride.
10. The use of the naphthalimide fluorescent dye according to claim 1 in palladium ion detection.

Description

Naphthalimide fluorescent dye and preparation method and application thereof Technical Field The invention relates to the technical field of fluorescent dyes, in particular to a naphthalimide fluorescent dye, and a preparation method and application thereof. Background Palladium is a noble metal that is widely used in industrial catalysts and electronic components, but its potential harm to human health is not negligible. Palladium and its compounds enter the body mainly by inhalation or skin contact, short term exposure may cause respiratory tract irritation such as cough, sore throat, and severe chemical pneumonia, and long term exposure may cause pulmonary fibrosis, affecting respiratory function. The cumulative effect of palladium also appears in skin allergic reactions, and contact dermatitis appears after some people wear ornaments containing palladium, and the symptoms are red swelling, itching and even ulceration. At the immune system level, palladium may interfere with leukocyte activity, impair body resistance, and increase risk of infection. The widespread use of palladium catalysts (e.g., palladium on carbon, palladium acetate) during drug manufacture may result in trace amounts of palladium remaining in the product, which may cause allergic reactions, organ toxicity, or long-term health risks. Therefore, the pharmacopoeia of each country sets strict limit requirements on palladium residue in the bulk drug, for example, the palladium residue amount is not more than ten parts per million (10 ppm) specified in the pharmacopoeia of China, so as to ensure the safety of the drug. Conventional detection methods mainly include Atomic Absorption Spectrometry (AAS) and inductively coupled plasma mass spectrometry (ICP-MS). The AAS quantifies by measuring the absorption of palladium atoms to light with specific wavelength, is simple and convenient to operate, but has lower sensitivity, and the ICP-MS has higher sensitivity and multi-element detection capability by utilizing a plasma ionization technology, and can accurately identify trace palladium residues. The assay procedure typically involves sample dissolution, filtration and instrumental analysis, such as sample introduction after dissolution of the drug substance in nitric acid, to reduce matrix interference. The choice of these methods requires a trade-off between cost, accuracy and practical requirements to meet drug quality control criteria. Particularly ICP-MS, the cost is extremely high, professional maintenance is needed, and the intermediate of some small and medium-sized bulk drugs is difficult to purchase and maintain. Therefore, the development of a simpler palladium ion detection means has more important significance for the quality control of bulk drugs. The fluorescent probe technology shows remarkable advantages in detection sensitivity by virtue of a unique fluorescent signal amplification mechanism, and has the core that the controllable change of fluorescence intensity, wavelength or service life is triggered by the specific combination of probe molecules and targets, and the signal conversion mechanism enables the weak concentration change of the targets to be accurately captured by an optical system. For example, in the single molecule detection field, the fluorescent probe can break through the physical limit of the traditional method, so that the picomolar or even femtomolar detection sensitivity is realized, and the possibility is provided for early disease marker screening. In summary, the invention aims at the problems existing in the prior art, develops a fluorescent dye and a preparation method thereof, and applies the fluorescent dye to detection of palladium ions in bulk drugs and chemical intermediates. Disclosure of Invention In order to overcome the defects of the prior art, the invention provides naphthalimide fluorescent dye applied to palladium ion detection and a preparation method thereof. The technical problems to be solved by the invention are realized by adopting the following technical scheme: The first object of the invention is to provide a naphthalimide fluorescent dye, which has the following structural formula: the second object of the invention is to provide a preparation method of the naphthalimide fluorescent dye, which comprises the following steps: S1, 4-bromo-1, 8-naphthalene dicarboxylic anhydride and n-butylamine undergo an acylation reaction to obtain an intermediate 1; s2, performing carbonylation reaction on the intermediate 1 and N, N-dimethylformamide to obtain an intermediate 2; S3, performing oxidation-reduction reaction on the intermediate 2 and hydroxylamine hydrochloride to obtain an intermediate 3; s4, carrying out substitution reaction on the intermediate 3 and 3-bromopropyne to obtain the naphthalimide fluorescent dye. The synthetic route is as follows: further, the molar ratio of the 4-bromo-1, 8-naphthalene dicarboxylic anhydride to the n-butylamine is 1 (1-2). The carbonylation re