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Film material for realizing photostimulation response through pi-conjugation regulation and control as well as preparation method and application

A thin-film material and light-stimulation technology, applied in luminescent materials, color-changing fluorescent materials, chemical instruments and methods, etc., can solve the problem of single-sided influence on performance, achieve cheap and easy availability, expand design ideas and application prospects, raw materials cheap effect

Pending Publication Date: 2021-11-12
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This strategy proves that the adjustment of π-conjugation can improve the performance of the material to a certain extent, but the effect on the performance is one-sided and single

Method used

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  • Film material for realizing photostimulation response through pi-conjugation regulation and control as well as preparation method and application
  • Film material for realizing photostimulation response through pi-conjugation regulation and control as well as preparation method and application
  • Film material for realizing photostimulation response through pi-conjugation regulation and control as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0072] Solution preparation of host molecule (I) polymethyl methacrylate (PMMA)

[0073] Weigh 10g PMMA and place it in a dry and clean 250mL round bottom flask, add 100mL tetrahydrofuran solvent, take a clean glass stopper to block the bottle mouth, and avoid solvent volatilization. After the sample is completely dissolved, a concentration of 100mg / mL of no color transparent solution.

Embodiment 2

[0075] S1. Synthesis of guest molecule (II) N,N-diphenyl-2-naphthylamine

[0076]

[0077] Weigh N,N-diphenyl-2-naphthylamine (2.19g, 10mmol), 2-bromonaphthalene (1.25mL, 12mmol), palladium acetate (112.6mg, 0.5mmol), tri-tert-butylphosphine (0.5mL , 0.25mmol) and potassium tert-butoxide (1.68g, 15mmol) in a 250mL reaction flask, vacuum-dried for 0.5h, added 80mL of anhydrous oxygen-free toluene solvent, heated to reflux under nitrogen protection, and stirred for 12h. After the reaction, it was extracted and washed with water, separated by silica gel column chromatography (eluent: petroleum ether:dichloromethane=7:3), and purified to obtain pure white solid (II) (2.52g, 85.3%). figure 1 show 1 H NMR (400MHz, CDCl 3 )δ7.75(d, J=8Hz, 1H), 7.71 (d, J=8.8Hz, 1H), 7.58(d, J=8Hz, 1H), 7.42(d, J=2.4Hz, 1H), 7.41 -7.32(m,2H),7.29-7.24(m,5H),7.13(dd,J 1 =7.6Hz,J 2 =1.2Hz,4H),7.04(tt,J 1 =8.6Hz,J 2 =1.2Hz,2H). figure 2 show 13 C NMR (100MHz, CDCl 3 )δ147.77, 145.45, 134.39...

Embodiment 3

[0081] S1. Synthesis of guest molecule (III) N-phenyl-2,2-dinaphthylamine

[0082]

[0083] The synthesis method of the guest molecule (III) is the same as that of the guest molecule (II). Figure 5 show 1 H NMR (400MHz, CDCl 3 )δ7.78(d, J=7.6Hz, 1H), 7.75(d, J=8.8Hz, 1H), 7.60(d, J=8Hz, 1H), 7.48(d, J=2.4Hz, 1H), 7.43-7.28(m,4H),7.19(dd,J 1 =9.6Hz,J 2 =1.2Hz,1H),7.08(tt,J 1 =8.4Hz,J 2 =1.2Hz,1H). Figure 6 show 13 C NMR (100MHz, CDCl 3 )δ147.71, 145.43, 134.41, 130.13, 129.33, 128.94, 127.56, 126.95, 126.28, 124.57, 124.54, 124.51, 123.13, 120.53. Figure 7 The HPLC spectrum is shown. Figure 8 Show HRMS (ESI) m / z calcd for C 22 h 18 N + (M+H) + 346.1551,found 346.1590.

[0084] S2. Weigh 5 mg of the guest molecule (III) in step S1, and put it into a clean and dry container.

[0085] S3. Measure 1 mL of the main body (I) solution in Example 1, dissolve the sample weighed in step S2 with a doping ratio of 5% by mass fraction, and disperse it evenly by ultra...

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PUM

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Abstract

The invention discloses a preparation method and application of a film material for realizing photostimulation response through pi-conjugation regulation and control. The preparation method comprises photoactivation phosphorescence and photochromism. According to the preparation method, the subject is polymethyl methacrylate (PMMA), and the objects are N, N-diphenyl-2-naphthylamine, N-phenyl-2, 2-dinaphthylamine and 2, 2, 2-trinaphthylamine respectively. According to the invention, guest molecules are doped in a subject PMMA solution according to a mass fraction of 5%, and the photostimulation response thin film material with photoactivation phosphorescence and photochromic behaviors is obtained through a solution volatilization method. Based on the characteristics, the thin film material can be applied to the fields of anti-counterfeiting, information encryption and decryption, erasable materials and the like, can also be used as optical discoloration sunglasses, and has the advantages of quick response, good light transmission, fatigue resistance and the like. The preparation method is simple, the raw materials are cheap and easy to obtain, the reaction steps are few, the yield is high, and a simple and effective design strategy is provided for developing a photoresponse material with photoactivation phosphorescence and photochromic characteristics through pi-conjugation regulation and control.

Description

technical field [0001] The present invention relates to the field of light-stimuli-responsive materials, in particular to a light-stimuli-responsive thin-film material, preparation method and application thereof that realize light-activated phosphorescence and photochromism through π-conjugation regulation. Background technique [0002] Functional organic π-conjugated molecules have attracted much attention due to their potential applications in optoelectronic devices such as organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs), memory devices, and stimuli-responsive devices. In general, rational molecular design is the key to achieve optimal optoelectronic properties, which are closely related to the molecular structure. At present, it is a hot research topic to study the influence of the π-conjugated structure of molecules on their related properties. In fact, most organic optoelectronic materials are based on π-conjugated small molecules and po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C09K11/02C09K11/06G02C7/10
CPCC09K9/02C09K11/025C09K11/06G02C7/102C09K2211/1011
Inventor 李振杨玉杰方曼曼杨杰
Owner TIANJIN UNIV
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