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Temperature fluorescent probe based on triaryl boron compound and its preparation and application

A compound, temperature-sensitive technology, applied in the direction of thermometers, thermometers, and compounds containing elements of Group 3/13 of the periodic table with physical/chemical changes, which can solve the problem of difficult to achieve in-situ detection in micro-areas and susceptible to environmental interference. , narrow application temperature and other problems, to achieve the effect of no correction, wide practical range, wide temperature measurement range

Active Publication Date: 2016-08-10
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Usually the first type of method is the most widely used type, but it is difficult to achieve micro-area (less than 10 microns) and in-situ detection; the probe obtained by applying the second type of design principle can only detect the surface temperature of the measured object , and the radiation frequency of the measured object needs to be determined; the third type of method is a method that has been studied more at present. It solves the defects of the first two types of methods to a certain extent, but it also has some defects. The thermochromic liquid crystal temperature measurement has the disadvantages of narrow application temperature and low sensitivity, and the application of fluorescence intensity ratio method is susceptible to environmental interference, etc.

Method used

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  • Temperature fluorescent probe based on triaryl boron compound and its preparation and application
  • Temperature fluorescent probe based on triaryl boron compound and its preparation and application
  • Temperature fluorescent probe based on triaryl boron compound and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Preparation of compound Ia, its reaction scheme is as follows:

[0069]

[0070] Slowly add 0.8mL (2.22M) n-butyl lithium dropwise into 20ml ether solution containing 480mg 1-bromopyrene at -78°C under the protection of nitrogen. Stirring was continued for 1 hour. Then cool down to-78°C again, slowly add 5ml of ether solution containing 240mg 2,4,6-triisopropylphenylboronic acid dimethyl ester dropwise to the above solution, continue to stir for 30 minutes after the dropwise addition is completed, and then return to to room temperature and stirred overnight. After the reaction was completed, it was washed with water and separated on a silica gel column (developing solvent: petroleum ether: dichloromethane = 5:1, volume ratio) to obtain 380 mg of the product with a yield of 72%. Compound Ia: 1 HNMR (400MHz, CDCl 3 )δ=8.23(d,J=7.74Hz,2H),8.20-8.15(m,6H),8.12(d,J=5.4Hz,2H),8.02(d,J=9.22Hz,2H),7.97( d,J=8.82Hz,4H),7.57(d,J=9.22Hz,2H),7.08(s,2H),3.03-2.96(m,1H),2.93-...

Embodiment 2

[0073] The intermediate Ih of compound Id is prepared, and its molecular structural formula is:

[0074]

[0075] Its reaction scheme is as follows:

[0076]

[0077] 100mg Tris(dibenzylideneacetone)dipalladium(0)chloroform adduct, 1.5g sodium tert-butoxide, 120mg bis-diphenylphosphonobinaphthyl

[0078] (2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl) and 1.80g of 1,6-dibromopyrene were added to 50ml of degassed toluene, stirred for 15 minutes under nitrogen protection, and then added 0.5ml tetrahydropyrrole, then slowly warming up to 90 ° C, continue to stir for 3 hours. After the reaction was completed, remove incompatible substances by filtration, wash with water three times, and separate on a silica gel column (petroleum ether: dichloromethane = 1:1, volume ratio) to obtain 910 mg of the product with a yield of 52%. Intermediate compound Ih: 1 H NMR (400MHz, CDCl 3 )δ=8.41(d,J=9.1Hz,1H),8.19(d,J=9.1Hz,1H),8.14(d,J=8.2Hz,1H),8.07(d,J=8.4Hz,1H) ,8.02(d,J=9.1Hz,1H),7...

Embodiment 3

[0080] Preparation compound Id, its reaction scheme is as follows:

[0081]

[0082] Compound Id was synthesized by the same method as that of Ia, and the yield was 66%. 1 H NMR (400MHz, CDCl 3 )δ=8.50(d,J=9.1Hz,2H),8.14(d,J=6.8Hz,2H),8.00(t,J=8.0Hz,4H),7.85(q,J=8.3Hz,4H) ,7.56(s,2H),7.43(d,J=8.5Hz,2H),7.06(s,2H),3.61(s,8H),2.98(t,J=6.7Hz 1H),2.91(t,J =5.7Hz,2H),2.11(s,8H),1.35(d,J=6.8Hz,6H),0.94(d,J=5.9Hz,6H),0.78(d,J=6.0Hz,6H); MALDI-TOF:M + 754.5; Elemental Analysis (C 55 h 55 BN 2 ): C 87.51%, H 7.34%, N 3.71%; measured: C 87.10%, H 7.26%, N 3.57%.

[0083] image 3 is the fluorescence spectrum of compound Id at different temperatures (350nm excitation), Figure 4 It is a chromaticity diagram converted from the spectrum diagram of compound Id. As the temperature increases, the luminescence of the compound gradually changes from orange to green.

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Abstract

The invention discloses a probe compound for detecting spectrum temperature and a micro-capsule thermometer. The compound is a special triarylborane compound, and the probe compound can be taken as a micro-capsule thermometer, which can be used for real-time detection of temperature under different environments, especially for in-situ detection of static and dynamic temperature of micro-area and large-area. The micro-capsule fluorescence thermometer, which is prepared from the compound, has the advantages of rapid and convenient measurement of temperature, adaptability for various complex environments, furthermore, the two modes of spectrum identification and color scale identification can be selected individually, which is beneficial for the detection of spectrometer and the detection of colorimeter.

Description

technical field [0001] The invention relates to a class of fluorescent microcapsule probes for detecting temperature based on triaryl boron compounds, especially fluorescent microcapsule probes for in-situ temperature detection of micro-regions and large areas. Background technique [0002] The boron atom in the center of triaryl boron compounds has strong electron-deficiency properties caused by empty p-π orbitals, and is often used as a strong π electron acceptor. When it interacts with adjacent conjugated organic π systems, it will Produces a strong delocalization effect, which makes it have some remarkable properties, such as the formation of charge transfer state from electron donor to central boron, high luminous efficiency in solution and solid state, etc. These properties make triaryl boron compounds have good optical and electrical properties, and have broad application prospects in the field of optoelectronics, such as photochemical sensors, emissive layers and ele...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C08L23/10C08L23/04C08L27/06C08L25/04C08K5/55C09D125/04C09D7/12C09D5/26G01K11/20
Inventor 杨国强冯娇王双青李沙瑜胡睿
Owner INST OF CHEM CHINESE ACAD OF SCI
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