Check patentability & draft patents in minutes with Patsnap Eureka AI!

Near-infrared naphthalimide dye as well as preparation method and application thereof

A technology of naphthalimide dye and naphthalimide, which is applied in the field of analytical chemistry, can solve the problems of instability, time-consuming, expensive instruments, etc., and achieve the effects of good stability, good water solubility and excellent optical properties

Active Publication Date: 2021-07-23
FUZHOU UNIV
View PDF2 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these techniques have advantages such as high selectivity and high sensitivity, they also have disadvantages such as instability and require expensive instruments and time-consuming operations.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Near-infrared naphthalimide dye as well as preparation method and application thereof
  • Near-infrared naphthalimide dye as well as preparation method and application thereof
  • Near-infrared naphthalimide dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] 2-(3,5,5-Trimethylcyclohex-2-en-1-ylidene)malononitrile Preparation of:

[0066] In a 50 mL two-necked round bottom flask, 1.90 g (13.7 mmol) of isophorone, 1.36 g (20.6 mmol) of malononitrile and 0.45 mL of piperidine were dissolved in 25 mL of ethanol, and refluxed at 78 ° C for 12 Hour. After the reaction, the mixture solution was poured into 50 mL of ice water, the precipitate was filtered, washed with water and dried in vacuo, purified on a silica gel column, and the eluent was PE:EA=8:1 (v:v) to obtain colorless crystals 1.52 g, yield 59%.

[0067] 1 H NMR (400MHz, CDCl 3 )δ6.62(s,1H),2.51(s,2H),2.17(s,2H),2.03(s,3H),1.01(s,6H)

Embodiment 2

[0069] Bromonaphthalimide Derivatives Preparation of:

[0070] In a 250 mL round bottom flask, 1.00 g (3.61 mmol) of 4-bromo-1,8-naphthalic anhydride and 1.30 mL of n-butylamine (13.0 mmol) were dissolved in 100 mL of ethanol, and refluxed at 78°C for 12 hours. After the reaction, the solvent ethanol was removed under reduced pressure, and the silica gel column was purified with the eluent PE:EA=12:1 (v:v) to obtain 0.84 g of white solid with a yield of 70%.

[0071] 1 H NMR (400MHz, CDCl 3 )δ8.65(d, J=7.2Hz, 1H), 8.56(d, J=8.5Hz, 1H), 8.41(d, J=7.9Hz, 1H), 8.04(d, J=7.8Hz, 1H) ,7.84(t,J=7.9Hz,1H),4.17(t,J=7.5Hz,2H),1.75-1.68(m,2H),1.50-1.40(m,2H),0.98(t,J=7.3 Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ163.44, 163.41, 133.00, 131.85, 131.04, 130.97, 130.41, 130.03, 128.78, 127.96, 123.03, 122.16, 40.35, 30.14, 20.37, 13.84; HRMS (ESI): Calcd for C 16 h 14 NO 2 Br([M+H] + ):332.0286,Found:332.0290.

Embodiment 3

[0073] Naphthalimide Derivatives Containing Methoxy Preparation of:

[0074] In the 100mL round bottom flask, the bromonaphthalimide derivative prepared by 0.66g (1.98mmol) embodiment 2 0.86g (15.9mmol) of sodium methoxide and 0.01g of anhydrous copper sulfate were dissolved in 50mL of methanol and refluxed at 65°C for 12 hours. After the reaction, the solvent methanol was removed under reduced pressure, purified by silica gel column, the eluent was PE:EA=4:1 (v:v), and 0.53 g of light yellow solid was obtained with a yield of 94%.

[0075] 1 H NMR (400MHz, CDCl 3 )δ8.57(d, J=7.3Hz, 1H), 8.52(d, J=8.3Hz, 2H), 7.67(t, J=7.8Hz, 1H), 7.01(d, J=8.3Hz, 1H) ,4.16(t,J=7.5Hz,2H),4.12(s,3H),1.75-1.68(m,2H),1.50-1.40(m,2H),0.98(t,J=7.4Hz,3H); 13 C NMR (100MHz, CDCl 3 )δ163.72, 163.10, 159.98, 132.55, 130.64, 128.39, 127.73, 125.25, 122.57, 121.67, 114.40, 104.62, 55.84, 39.72, 30.05, 20.28, 13.74; HRMS (ESI C): Calcd 17 h 18 NO 3 ([M+H] + ):284.1287,Found:284.1289.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention belongs to the field of analytical chemistry, and particularly relates to a near-infrared naphthalimide dye as well as a preparation method and an application thereof, and the near-infrared naphthalimide dye is prepared by taking a naphthalimide derivative containing an aldehyde group and a hydroxyl group, 2-(3, 5, 5-trimethylcyclohex-2-ene-1-subunit) malononitrile and 4-bromobutyryl chloride as raw materials. The near-infrared naphthalimide dye has good stability and excellent optical performance, and especially, the introduced malononitrile and 4-bromobutyl groups can enhance the fluorescence emission of the dye. When the near-infrared naphthalimide dye is used for detecting human serum albumin (HSA), the human serum albumin can be mutually combined with dye molecules to initiate the change of absorption spectrum and fluorescence spectrum of the dye, so that the near-infrared naphthalimide dye can be used as a fluorescence probe for detecting the HSA, is used for fluorescence detection of the HSA in urine, and has good detection sensitivity.

Description

technical field [0001] The invention belongs to the field of analytical chemistry, and in particular relates to a near-infrared naphthalimide dye, a preparation method thereof and its application in the fluorescence detection of human serum albumin. Background technique [0002] Human serum albumin (HSA) is the main carrier protein in human plasma and plays a crucial role in facilitating the transport of various drugs, fatty acids and metabolites. The content of HSA in body fluids is generally regarded as a reliable indicator of health, and the normal concentration of HSA in urine is less than 30mg L -1 , while in serum, the normal range of HSA concentration is about 35-55g L -1 . For example, low levels of HSA in serum are called hypoalbuminemia, which may indicate liver failure, cirrhosis, or chronic hepatitis. Conversely, the presence of too much HSA in the urine can lead to microalbuminuria, which can indicate kidney disease, cardiovascular disease, and diabetes. The...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/08C09K11/06C07D221/14G01N21/64
CPCC09B57/08C09K11/06C07D221/14G01N21/6428C09K2211/1007C09K2211/1029G01N2021/6432Y02E10/542
Inventor 傅南雁柯越
Owner FUZHOU UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com