Cyanodiphenylethylene compound with stable Z/E configuration in excited state and preparation method and application thereof

A technology for cyanodiphenylethylene and compounds, which is applied in the field of cyanodiphenylethylene compounds, can solve the problems of small steric hindrance, difficulty in obtaining Z/E isomers, etc., and achieves the effect of broad application prospects

Inactive Publication Date: 2019-01-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the cyanodiphenylvinyl group is only bonded with one cyano group and two phenyl groups at three positions of the double bond, it is less sterically hindered and more l

Method used

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  • Cyanodiphenylethylene compound with stable Z/E configuration in excited state and preparation method and application thereof
  • Cyanodiphenylethylene compound with stable Z/E configuration in excited state and preparation method and application thereof
  • Cyanodiphenylethylene compound with stable Z/E configuration in excited state and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] The synthesis of embodiment 1 I-a and II-a

[0058] (1) Under nitrogen protection, phenoxazine (V-a, 1.83g, 10mmol), 4-bromophenylacetonitrile (V-b, 2.28g, 12mmol), palladium acetate (0.13g, 0.6mmol), three (tert-butyl ) Phosphine (0.53g, 2.6mmol) and sodium tert-butoxide (2.50g, 26mmol) were dissolved in toluene (30mL), and the system was heated to 115°C for reflux for 24 hours. After the system was cooled, it was extracted with deionized water and dichloromethane, and the obtained organic phase was added with anhydrous MgSO 4 After drying, concentrate under reduced pressure, then separate and purify by column chromatography, the stationary phase is 300-400 mesh silica gel, the mobile phase is dichloromethane / petroleum ether (volume ratio 1:3), and finally the intermediate product V-c is obtained as a white solid 1.48 g, 50% yield. 1 H NMR (500MHz, CDCl 3 )δ (TMS, ppm) 7.59 (d, J = 8.4Hz, 2H), 7.40 (d, J = 8.2Hz, 2H), 6.74-6.57 (m, 6H), 5.90 (d, J = 7.6Hz, 2H ), 3....

Embodiment 2

[0062] The synthesis of embodiment 2 I-b and II-b

[0063] The synthetic method is the same as in Example 1, except that in step (2), 4-trifluoromethylbenzaldehyde is replaced by benzaldehyde (0.1g, 1mmol), and finally the target product I-b (0.32g, yield 83 %), II-b (0.02 g, yield 5%). The characterization structure of the confirmed substance is as follows:

[0064] I-b: 1 H NMR (500MHz, CDCl 3 )δ(TMS,ppm)7.90-7.99(m,4H),7.64(s,1H),7.49-7.56(m,3H),7.47(d,J=8.5Hz,2H),6.73(dd,J= 8.5Hz, J=1.7Hz, 2H), 6.66 (dt, J=15.2Hz, J=7.3Hz, 4H), 5.98 (dd, J=7.9Hz, J=1.4Hz, 2H). MALDI-TOF MS theoretical value (C 27 h 18 N 2 (0) m / z: 386.4, found: 387.4.

[0065] II-b: 1 H NMR (500MHz, CDCl 3 )δ (TMS, ppm) 7.62 (d, J = 8.4Hz, 2H), 7.48 (s, 1H), 7.33-7.40 (m, 3H), 7.30 (t, J = 7.4Hz, 2H), 7.24 (d , J=7.3Hz, 2H), 6.59-6.77 (m, 6H), 5.97 (d, J=7.8Hz, 2H). MALDI-TOF MS theoretical value (C 27 h 18 N 2 (0) m / z: 386.4, found: 387.4.

Embodiment 3

[0066] The synthesis of embodiment 3 I-c and II-c

[0067] (1) Under nitrogen protection, phenoxazine (V-a, 1.83g, 10mmol), p-bromoiodobenzene (3.39g, 12mmol), cuprous iodide (0.04g, 0.22mmol), sodium tert-butoxide (2.11 g, 22mmol) and cyclohexanediamine (0.13g, 1.1mmol), were dissolved in ultra-dry 1,4-dioxane (30ml), and the system was heated to 110°C and refluxed for 6 hours. After the system was cooled, it was extracted with deionized water and dichloromethane, and the obtained organic phase was added with anhydrous MgSO 4 After drying, it was concentrated under reduced pressure, and then separated and purified by column chromatography. The stationary phase was 300-400 mesh silica gel, and the mobile phase was dichloromethane / petroleum ether (volume ratio 1:9), and finally the intermediate product VI was obtained as a white solid. -a 2.27g, yield 67%. The characterization structure of the confirmed substance is as follows:

[0068] 1 H NMR (500MHz, CDCl 3 )δ (TMS, ppm...

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Abstract

The invention provides cyanodiphenylethylene compound with stable Z/E configuration in excited state and a preparation method and application thereof. The cyanodiphenylethylene compound with stable Z/E configuration in excited state acts as a novel light-emitting isomer; the structure can be controlled by introducing different push-pull electron groups so as to adjust light emission color and efficiency of the isomer; therefore, the cyanodiphenylethylene compound has a very promising application prospect in the fields, such as photoluminescence, piezochromism and fluorescent sensing.

Description

(1) Technical field [0001] The invention relates to a cyanodiphenylethylene compound with a stable Z / E configuration in an excited state, a preparation method thereof, and an application as a photoluminescence material. (2) Background technology [0002] With the rapid development of the national economy and the continuous improvement of people's living standards, more and more organic light-emitting materials have jumped into people's field of vision. The light-emitting materials with excellent performance are widely used in scientific research and development in display technology, medical imaging, anti-counterfeiting, etc. The field of people's livelihood. Studies have found that many molecular structures formed by substituting aromatic groups for double bond units can exhibit excellent luminescent properties, and have broad application prospects in the fields of biological probes, chemical sensing, optoelectronic devices, and stimulus responses. [0003] It is well know...

Claims

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Application Information

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IPC IPC(8): C07D265/38C09K11/06
CPCC07D265/38C09K11/06C09K2211/1007C09K2211/1033
Inventor 董玉杰许晨东宋庆宝
Owner ZHEJIANG UNIV OF TECH
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