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Diphenyl sulfone-based A-pi-D-pi-A type sensitizer as well as preparation method and application thereof

A technology of diphenyl sulfone and sensitizer, applied in the field of A-π-D-π-A type sensitizer and its preparation, can solve the problem of mismatch of absorption wavelength of photoinitiator, achieve fast photobleaching, excellent Effects of Intramolecular Charge Transfer Capability

Inactive Publication Date: 2019-07-16
安庆北化大科技园有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved by the present invention is that the wavelength provided by the visible LED light source in the prior art does not match the absorption wavelength of the photoinitiator. -Type A sensitizer

Method used

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  • Diphenyl sulfone-based A-pi-D-pi-A type sensitizer as well as preparation method and application thereof
  • Diphenyl sulfone-based A-pi-D-pi-A type sensitizer as well as preparation method and application thereof
  • Diphenyl sulfone-based A-pi-D-pi-A type sensitizer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] like figure 1 Shown, N-dodecyl-3,7-dibromophenothiazine (17.86g, 40mmol), CuI (0.7618g, 4mmol), PPh 3 (1.0492g, 4mmol), Pd(PPh 3 ) 2 Cl 2 (0.2808g, 0.4mmol) were mixed, 100mL DMF and 50mL triethylamine were added, stirred magnetically under nitrogen atmosphere, heated to 60°C and kept for 1h, then heated to 85°C. Then 2-methyl-3-butyn-2-ol was added dropwise, and the first product was obtained after reacting for 6 hours. During the reaction, the progress of the reaction was monitored by thin-layer chromatography. After the first product was cooled to room temperature, it was extracted with dichloromethane, and the organic phases were combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, purified through a silica gel column with ethyl acetate / petroleum ether as the eluent, and used Dissolve 150mL of isopropanol, add 10 molar equivalents of KOH, stir and heat to reflux for 4 hours under nitrogen atmosphere, after cooling to room tempera...

Embodiment 2

[0056] like image 3 As shown, the difference from Example 1 is that the reaction compound of this example is N-dodecyl-3,6-dibromocarbazole.

[0057] The intermediate is N-dodecyl-3,6-diethynylcarbazole.

[0058] H NMR spectrum characterization data of the intermediate:

[0059] 1 H NMR (400MHz, DMSO-d 6 )δ (ppm): 8.40 (d, J = 1.4Hz, 2H), 7.64 (s, 1H), 7.62 (s, 1H), 7.56 (dd, J = 8.4, 1.6Hz, 2H), 4.40 (t, J=7.0Hz, 2H), 1.73(q, J=7.1Hz, 2H), 1.27-1.12(m, 18H), 0.84(t, J=6.8Hz, 3H).

[0060] Carbon NMR spectrum characterization data of the intermediate:

[0061] 13 C NMR (DMSO-d 6 )δ (ppm): 140.19, 129.68, 124.53, 121.56, 112.24, 109.93, 84.66, 78.69, 42.44, 31.25, 28.91, 28.81, 28.79, 28.63, 28.37, 26.27, 22.05, 13.91%. Yield: 7

[0062] The final product is N-dodecyl-3,6-di(4-phenylsulfonylphenylethynyl)carbazole (C-DSO).

[0063] C-DSO H NMR spectrum characterization data:

[0064] 1 H NMR (400MHz, DMSO-d 6 )δ8.53(s,2H),8.12-7.90(m,8H),7.86-7.57(m,14H),4.43(t,J=7...

Embodiment 3

[0069] like Figure 5 As shown, the difference from Example 1 is that the reaction compound of this example is 4,4'-dibromotriphenylamine.

[0070] The intermediate is 4,4'-diethynyltriphenylamine.

[0071] H NMR spectrum characterization data of the intermediate:

[0072] 1 H NMR (400MHz, DMSO-d 6 )δ7.42-7.33(m,6H),7.20-7.14(m,1H), 7.11-7.06(m,2H),6.99-6.91(m,4H),4.09(s,2H).

[0073] Carbon NMR spectrum characterization data of the intermediate:

[0074] 13 C NMR (400MHz, d 6-DMSO) δ147.00, 145.88, 133.11, 132.99, 132.69, 129.89, 125.55, 124.68, 123.30, 122.83, 115.58, 83.39, 80.03. Yield: 62%.

[0075] The final product is 4,4'-bis(4-benzenesulfonylphenylethynyl)triphenylamine (T-DSO).

[0076] T-DSO H NMR spectrum characterization data:

[0077] 1H NMR (400MHz, Chloroform-d) δ (ppm): 7.99-7.92 (m, 4H), 7.92-7.86 (m, 4H), 7.59 (dd, J = 8.3, 1.7Hz, 5H), 7.57-7.47 ( m,5H),7.44-7.36(m,4H),7.34-7.28(m,2H),7.16-7.10(m,3H),7.09-7.00(m,4H).

[0078] Carbon spectrum chara...

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Abstract

The invention discloses a diphenyl sulfone-based A-pi-D-pi-A type sensitizer, relates to the field of photocurable materials, and aims to solve the problem that a wavelength provided by a visible LEDlight source is not matched with an absorption wavelength of a photoinitiator. The sensitizer provided by the invention uses carbazole, phenothiazine and triphenylamine groups having good electron donating properties and sensitizing properties as cores, and a diphenyl sulfone structure having strong electron absorption properties is bonded through a carbon-carbon triple bond, so that the A-pi-D-pi-A type sensitizer has good intramolecular charge transfer properties, and is used for sensitizing an aryl onium salt, thereby initiating free radical polymerization and cationic polymerization. The invention also discloses a preparation method of the diphenyl sulfone-based A-pi-D-pi-A type sensitizer. The method provided by the invention has simple and mild reaction conditions, and the product iseasy to purify. The invention also discloses an application of the diphenyl sulfone-based A-pi-D-pi-A type sensitizer. The diphenyl sulfone-based A-pi-D-pi-A type sensitizer is applied to a two-component photoinitiator system of the visible LED light source.

Description

technical field [0001] The invention relates to the field of photocurable materials, in particular to an A-π-D-π-A type sensitizer and a preparation method and application thereof. Background technique [0002] Photocuring has developed rapidly in the fields of coatings, electronic packaging, 3D printing, adhesives, and photoresists due to its advantages of greenness, low energy consumption, and rapid curing at room temperature. With the maturity of LED technology and the increasing pressure of environmental protection, it has become the development trend of the current light curing technology to replace the ultraviolet light source with high energy consumption, heavy pollution and great harm by LED light source. [0003] Most traditional photoinitiators have no activity in the visible light region, so the development of initiators or initiator systems suitable for visible LED light sources has always been a research hotspot and difficulty in the field of photocuring. In ad...

Claims

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Application Information

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IPC IPC(8): C08G59/68C08F2/48C08F122/14C08F122/20C07D209/86C07D279/22C07C317/36C07C315/04
CPCC07C315/04C07C317/36C07D209/86C07D279/22C08F2/48C08F122/14C08F122/20C08G59/68
Inventor 王涛贾小琴
Owner 安庆北化大科技园有限公司
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