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Method for preparing hemicyanine plastocyanin temperature-sensitive molecular optical probe containing electron-donating group

A technology of electron-donating groups and optical probes, which is applied in the field of preparation of temperature-sensitive molecular optical probes, 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-measuring instruments require electrical connections, which greatly limits their applications in areas such as high-speed moving objects and biomedical diagnostics

Method used

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  • Method for preparing hemicyanine plastocyanin temperature-sensitive molecular optical probe containing electron-donating group
  • Method for preparing hemicyanine plastocyanin temperature-sensitive molecular optical probe containing electron-donating group
  • Method for preparing hemicyanine plastocyanin temperature-sensitive molecular optical probe containing electron-donating group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of 2-methoxyphenylvinylindoline tetrafluoroborate (3a)

[0024]

[0025] Weigh 0.34g (0.0025mol) of o-methoxybenzaldehyde and place it in a 50mL round bottom flask, add 0.65g (0.0025mol) of N-methyl-2,3,3-trimethyl-3H-indolium iodide mol) and 25mL absolute ethanol, oil bath, stirring, react at 100°C for 12 hours, then add 0.41g potassium tetrafluoroborate, 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 0.57 g of red crystals with a yield of 72%. mp.212-214°C; ESI: m / z[M-BF 4 - ] + :292.1696; 1 H NMR (CDCl 3 ,400MHz), δ (ppm) 1.87 (s, 6H), 4.03 (s, 3H), 4.47 (s, 3H), 7.01-6.99 (d, J=8.4Hz, 1H), 7.21-7.17 (t, J =7.6Hz, 1H), 7.60-7.58 (t, J=5Hz, 4H), 7.70-7.69 (d, J=7.2Hz, 1H), 7.87-7.83 (d, J=16.4Hz, 1H), 8.40- 8.38 (d, J=8Hz, 1H), 8.64-8.60 (d, J=16.4Hz,...

Embodiment 2

[0033] Example 2: Synthesis of 3-methoxyphenylvinylindoline tetrafluoroborate (3b)

[0034]

[0035] Weigh 0.36g (0.0026mol) of m-methoxybenzaldehyde and place it in a 50mL round bottom flask, add 0.65g (0.0026mol) of N-methyl-2,3,3-trimethyl-3H-indolium iodide mol) and 25mL absolute ethanol, oil bath, stirring, react at 100°C for 12 hours, then add 0.37g 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 0.98 g of purple-black crystals with a yield of 98%. m.p.192-194°C; ESI: m / z[M-BF 4 - ] + Calculated value: 292.17; Measured value: 292.1696; 1 H NMR (CDCl 3 ,400MHz), δ (ppm) 1.89 (s, 6H), 4.03 (s, 3H), 4.53 (s, 3H), 7.16-7.14 (t, J=4.2Hz, 1H), 7.46-7.42 (t, J =8Hz, 1H), 7.61-7.59 (d, J=6Hz, 4H), 7.69-7.61 (d, J=1.6Hz, 2H), 7.86-7.82 (d, ...

Embodiment 3

[0037] Example 3: Synthesis of 4-methoxyphenylvinylindoline tetrafluoroborate (3c)

[0038]

[0039] Weigh 0.36g (0.0026mol) of p-methoxybenzaldehyde and place it in a 50mL round bottom flask, add 0.79g of N-methyl-2,3,3-trimethyl-3H-indolium iodide ( 0.0026mol) and 25mL absolute ethanol, oil bath, stirring, react at 100°C for 12 hours, then add 0.35g 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 0.96 g of red crystals with a yield of 96%. mp.208-210°C; ESI: m / z[M-BF 4 - ] + :292.1696; 1 H NMR (CDCl 3 ,400MHz), δ (ppm) 1.82 (s, 6H), 3.89 (s, 3H), 4.41 (s, 3H), 7.05-7.03 (d, J=8.8Hz, 2H), 7.52-7.51 (m, J =2.3Hz, 2H), 7.56-7.55 (t, J=2.4Hz, 2H), 7.75-7.71 (d, J=9.6Hz, 1H), 8.21-8.14 (m, J=9.2Hz, 3H); 13 C NMR (DMSO-d 6 ,100MHz), δ(ppm)...

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Abstract

A method for preparing a hemicyanine plastocyanin temperature-sensitive molecular optical probe containing an electron-donating group comprises the following steps of: 1) mixing the iodate of an indoline derivative and aromatic aldehyde in a molar ratio of 1: 1, and reflowing for 10-15 hours in ethanol; 2) adding KBF4 and reflowing for 2 hours for anion exchange; and 3) recrystallizing by using absolute ethyl alcohol to obtain the pure product of the hemicyanine plastocyanin temperature-sensitive molecular optical probe containing the electron-donating group. The method provided by the invention has the following advantage that the hemicyanine plastocyanin temperature-sensitive molecular optical probe containing the electron-donating group, obtained by the method, can be used for quickly measuring and monitoring the temperature of the fluid industrial production line by arranging ultraviolet absorption or fluorescence emission spectrum detection monitoring points at different parts. When the hemicyanine plastocyanin temperature-sensitive molecular optical probe containing the electron-donating group is used for carrying out the fluorescent mark on a living animal, imaging detection on the body temperature of the living animal can be realized by the fluorescence imaging technology; therefore, the optical probe has the potential of being applied to the fields of biomedical diagnosis and the like.

Description

【Technical field】 [0001] The invention relates to the preparation of temperature-sensitive molecular optical probes in optical sensing and detection technology, in particular to a preparation method of temperature-sensitive molecular optical probes based on electron-donating substituent hemicyanine. 【Background technique】 [0002] Temperature is an important parameter to describe the basic properties of substances. In the environment, meteorology, scientific research and many industrial productions, it is necessary to accurately measure the temperature of the acting object. In industrial production, real time temperature measurement is of great significance to optimize production process, improve product qualification rate and energy consumption. Common temperature measurement methods are mainly the direct contact method, including the use of mercury thermometers, thermocouples, thermistors, and thermistor temperature detectors. With the exception of liquid-scale thermomete...

Claims

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Application Information

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IPC IPC(8): C07D209/12C09K11/06G01K11/00
Inventor 曾宪顺刘畅王庆
Owner TIANJIN UNIVERSITY OF TECHNOLOGY
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