Preparation method for electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe

A technology of electron-withdrawing groups and optical probes, which is applied in the field of preparation of temperature-sensitive molecular optical probes containing electron-withdrawing groups hemicyanine, can solve problems such as limited applications, and achieve rapid measurement and monitoring effects

Inactive Publication Date: 2013-05-22
TIANJIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

With the exception of liquid-scale thermometers such as mercury thermometers, many temperature-determining instruments

Method used

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  • Preparation method for electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe
  • Preparation method for electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe
  • Preparation method for electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of 4-nitrophenylvinylindoline tetrafluoroborate (3a):

[0024]

[0025] Weigh 0.38g (0.0025mol) of p-nitrobenzaldehyde and place it in a 50mL round bottom flask, add 0.75g (0.0025mol) of N-methyl-2,3,3-trimethyl-3H-indolium iodide ) and 15mL of absolute ethanol, oil bath, stirring, and react at 100°C for 14 hours; then add 0.35g potassium tetrafluoroborate to the flask, and react for 2 hours; spin the solution to dryness, dissolve the solid in 5mL of DMF, and filter to remove inorganic salts , the obtained solution was spin-dried, and the solid was recrystallized with 10 mL of ethanol to obtain 0.52 g of orange crystals, with a yield of 52%. mp.228-230°C; ESI: m / z[M-BF 4 - ] + :307.1441; 1 H NMR (DMSO-d 6 ,400MHz), δ (ppm) 1.86 (s, 6H), 4.27 (s, 3H), 7.73-7.71 (m, J=2.2Hz, 2H), 7.94-7.90 (d, J=16.4Hz, 2H), 8.03-8.01 (t, J=4.4Hz, 1H), 8.46-8.43 (d, J=8.8Hz, 2H), 8.54-8.50 (m, J=16.4Hz, 3H); 13 C NMR (DMSO-d 6 ,100MHz), δ(ppm) 182.73, 150.0...

Embodiment 2

[0032] Example 2: Synthesis of 2,4-dinitrophenylvinylindoline tetrafluoroborate (3b):

[0033]

[0034] Weigh 0.29g (0.0015mol) of 2,4-dinitrobenzaldehyde into a 50mL round bottom flask, add 0.45 g (0.0015mol) and 15mL of absolute ethanol, oil bath, stirring, react at 100°C for 10 hours; then add 0.30g potassium tetrafluoroborate to the flask, and react for 2 hours. The solution was spin-dried, the solid was dissolved in 5 mL of DMF, the inorganic salt was removed by filtration, the obtained solution was spin-dried, and the solid was recrystallized with 10 mL of ethanol to obtain 0.22 g of dark red crystals with a yield of 33%. mp.214-216°C; ESI: m / z[M-BF 4 - ] + :352.1292; 1 H NMR (DMSO-d 6 ,400MHz), δ (ppm) 1.85 (s, 6H), 4.29 (s, 3H), 7.75-7.73 (t, J=3.6Hz, 2H), 7.86-7.82 (d, J=16.4Hz, 1H), 7.97-7.95 (t, J=4.2Hz, 1H), 8.06-8.04 (t, J=4.4Hz, 1H), 8.53-8.51 (d, J=8.4Hz, 1H), 8.80-8.77 (m, J= 8.4Hz, 2Hz, 2H), 8.91-8.90 (d, J=2Hz, 1H); 13 C NMR (DMSO-d 6 ,100MHz), δ(...

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Abstract

The invention relates to a preparation method for an electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe. The preparation method comprises the following steps of: 1) mixing iodate of a raw material indoline derivative and aromatic aldehyde by molar ratio of 1:1, and performing reflux in ethanol for 10-15 hours; 2) adding KBF4 and performing reflux for 2 hours for anion exchange; and 3) obtaining the semi-cyanine temperature-sensitive molecular optical probe through recrystallization of absolute ethyl alcohol. The preparation method provided by the invention has the advantages that the electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe material can quickly determine and monitor temperature of a fluid industrial production line by arranging ultraviolet absorption or fluorescence emission spectrum detection monitoring points; and through fluorescence labeling of living animals by the electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe, image detection for body temperature of the living animals can be realized through fluorescence imaging technology, so that the electrondrawing group containing semi-cyanine temperature-sensitive molecular optical probe can be applied to fields of biomedical diagnosis and the like.

Description

【Technical field】 [0001] The invention relates to the preparation of a temperature-sensitive molecular optical probe in optical sensing and detection technology, in particular to a preparation method of a semicyanine temperature-sensitive molecular optical probe containing an electron-withdrawing group. 【Background technique】 [0002] Temperature is an important parameter to describe the basic properties of substances. In many scientific researches and industrial productions, it is necessary to accurately measure the temperature of the acting object. In industrial production, in order to optimize the production process, reduce by-products and energy consumption, real-time temperature measurement is of great significance. The common temperature measurement method is to use contact thermometers, such thermometers include mercury thermometers, thermocouples, thermistors, thermal resistance temperature detectors, etc. With the exception of liquid-scale thermometers such as merc...

Claims

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Application Information

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IPC IPC(8): C07D209/10C09B23/14G01K11/30
Inventor 曾宪顺刘畅王庆
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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