Tetraphenylethylene macrocyclic compound with mechanofluorescent color-changing performance, synthesis method and use

A technology of macrocyclic compounds and tetraphenylethylene, applied in chemical instruments and methods, organic chemistry, color-changing fluorescent materials, etc., can solve problems such as non-luminescence, limited applications, and weakened fluorescence

Inactive Publication Date: 2021-04-20
SOUTH CHINA NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Due to the fact that the fluorescence of traditional fluorescent molecules will weaken at high concentrations, or even not emit light, thus limiting their applications in the fields of display devices, sensors, and optical devices

Method used

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  • Tetraphenylethylene macrocyclic compound with mechanofluorescent color-changing performance, synthesis method and use
  • Tetraphenylethylene macrocyclic compound with mechanofluorescent color-changing performance, synthesis method and use
  • Tetraphenylethylene macrocyclic compound with mechanofluorescent color-changing performance, synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] In a 250 mL round bottom flask, 2-bromo-1,1,2-triphenylethylene (3.3524 g, 10 mmol), 3,5-dimethoxyphenylboronic acid (2.731 g, 15 mmol), tetra-n-butyl bromide Ammonium (0.3224g, 1mmol), potassium carbonate (4.976g, 36mmol, first dissolved in 18mL water) and Pd (PPh 3 ) 4 (0,01g, 0.001mmol) dissolved in 60mL toluene, airtight, N 2 Gas was washed three times, and the mixture was stirred and refluxed for 12 hours at 95°C. DCM was added for dilution, the organic layer was washed with water and saturated brine respectively, and the organic layer was dried over anhydrous sodium sulfate. Column chromatography with petroleum ether:ethyl acetate (V:V=20:1) gave a white solid as shown in Formula 11, namely TPE-OMe, with a yield of 98.7%.

[0048] NMR spectrum of TPE-OMe: 1 H NMR (600MHz, CDCl3) δ7.20–7.00(m, 15H), 6.25(d, J=1.8Hz, 1H), 6.21(d, J=1.8Hz, 2H), 3.56(s, 6H). 13 C NMR (151MHz, CDCl 3 )δ=159.95,145.52,143.91,143.57,143.24,141.07,140.90,131.31,131.25,130.96,127.76,...

Embodiment 2

[0051] Add TPE-OMe (3.9218g, 10mmol) to 150mL DCM in 300mL, then add 3.6mL boron tribromide (BBr 3 ) was slowly dropped into it, and after the drop was completed, the temperature was raised to room temperature, and stirred for 12h. DCM was added for dilution, the organic layer was washed with water and saturated brine respectively, and the organic layer was dried over anhydrous sodium sulfate. Column chromatography with petroleum ether:ethyl acetate (V:V=5:1) gave a white solid as shown in Formula 12, namely TPE-OH, with a yield of 100.0%.

[0052] NMR spectrum of TPE-OH: 1 H NMR (600MHz, DMSO) δ9.00(s, 2H), 6.93-7.12(m, 15H), 5.96(s, 1H), 5.89(d, J=1.3Hz, 2H). 13 C NMR (151MHz, CDCl 3 )δ157.97, 148.13, 145.49, 145.41, 145.20, 143.16, 142.01, 133.26, 133.16, 133.02, 129.72, 129.66, 129.62, 128.67, 128.49, 113.14, 103.30. HRMS: C 26 h 20 o 2 for [M]+, calculated 364.1463, found 364.1464.

[0053]

Embodiment 3

[0055] 2,2,3,3-tetrafluoro-1,4-butanediol (4.0000 g, 24.68 mmol), 2,2,3,3,4,4-hexafluoro-1, 5-pentanediol (5.2386g, 24.68mmol) or 2,2,3,3,4,4,5,5-octafluoro-1,6-hexanediol (6.4667g, 24.68mmol) was added to 75mL DCM Cool to 0°C, add 5 mL of pyridine, stir for 10 minutes, then slowly drop trifluoromethanesulfonic anhydride (12.5 mL, 74.04 mmol) into it, warm to room temperature after dropping, and stir for 12 h. DCM was added to dilute, washed with water and saturated brine respectively, then dried with anhydrous sodium sulfate, and spin-dried to obtain white solid 4F-OTf, oil 6F-OTf and white solid 8F-OTf, respectively, with a yield of 100.0%.

[0056] NMR spectrum of compound 4F-OTf: 1 H NMR (600MHz, CDCl 3 )δ5.06–4.60(m,4H). 19 F NMR (565MHz, CDCl3) δ -74.06, -120.47.

[0057] The nuclear magnetic spectrum of compound 6F-OTf: 1 H NMR (600MHz, DMSO) δ5.50 (s, 4H). 19 F NMR (565MHz, DMSO) δ-75.14, -119.75, -124.26.

[0058] The NMR spectrum of compound 8F-OTf: 1 H NMR (...

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Abstract

The invention discloses a tetraphenylethylene macrocyclic compound with mechanofluorescent color-changing performance. The compound connects alkyl chain structural units through its own strong fluorescence property, so that it has the performance of fluorescence color difference before and after the pressure of the solid is increased, and can be used as Fluorescent probes recognize cyclic carboxylic acids. Described tetraphenylethylene macrocyclic compound, its structural formula is as shown in formula 1 or formula 2: in the formula: connecting bridge R is 1,4-butylene (-(CH 2 ) 4 ‑), 2,2,3,3‑tetrafluoro‑1,4‑butylene (‑CH 2 (CF 2 ) 2 CH 2 ‑), 1,5‑pentylene (‑(CH 2 ) 5 ‑), 2,2,3,3,4,4‑hexafluoro‑1,5‑pentylidene (‑CH 2 (CF 2 ) 3 CH 2 ‑), 1,6‑hexylene (‑(CH 2 ) 6 ‑) or 2,2,3,3,4,4,5,5‑octafluoro‑1,6‑hexylene (‑CH 2 (CF 2 ) 4 CH 2 -).

Description

technical field [0001] The invention relates to the field of organic solid fluorescent mechanochromic materials, in particular to a tetraphenylethylene macrocyclic compound with mechanofluorochromic properties, a synthesis method and an application thereof. Background technique [0002] Due to the fact that the fluorescence of traditional fluorescent molecules will weaken at high concentrations, or even not emit light, thus limiting their applications in the fields of display devices, sensors, and optical devices. The phenomenon of weakened fluorescence and non-luminescence of traditional fluorescent molecules under aggregation conditions is called the "concentration quenching" effect, also known as "aggregation-caused quenching (ACQ)". With the rapid development of modern science and technology, it is urgent to make breakthroughs in fluorescent materials. [0003] In 2001, Tang Benzhong's research group reported that some silole molecules hardly emit light in solution, but...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D323/00C09K11/06C09K9/02
Inventor 曾卓张梅何展宇
Owner SOUTH CHINA NORMAL UNIVERSITY
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