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Triphenyl amine-naphthalin multi-branched molecule having two-photon polymerization initiation characteristic

A two-photon polymerization and triphenylamine technology, applied in the field of triphenylamine-naphthalene multi-branch molecules, can solve the problems of low polymerization efficiency, small two-photon absorption cross-section, low photosensitivity, etc. The effect of high microstructure fineness and low aggregation threshold

Inactive Publication Date: 2009-01-21
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are no commercial products for efficient two-photon polymerization initiators. Although the use of traditional ultraviolet photoinitiators (such as Benzil) to initiate polymerization of resins in three-dimensional microfabrication has been reported, due to the small two-photon absorption cross-section of the initiator molecules, Leads to low polymerization efficiency, low photosensitivity, and low resolution of the polymerization system

Method used

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  • Triphenyl amine-naphthalin multi-branched molecule having two-photon polymerization initiation characteristic
  • Triphenyl amine-naphthalin multi-branched molecule having two-photon polymerization initiation characteristic
  • Triphenyl amine-naphthalin multi-branched molecule having two-photon polymerization initiation characteristic

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Example 1: Synthesis of 4,4',4"-tris(4-bromo-1-naphthylvinyl)triphenylamine.

[0032] (1) Preparation of 4,4',4"-triphenylamine trialdehyde: under a nitrogen atmosphere, first place 2.4g (0.62mol) of 4,4',4"-triphenylamine tribromide in a three-necked flask, seal the After degassing, 30 mL of dry THF was injected, 3.5 mL of dry DMF was injected at -78°C, and 15.6 mL of n-butyllithium was injected dropwise with stirring. After dropping, react at -78°C for 3 hours, then react at room temperature for 3 hours, stop the reaction, and pour the reaction solution into NH 4 Cl saturated aqueous solution, CH 2 Cl 2 After extraction, the organic layer was separated, concentrated and reprecipitated with petroleum ether to obtain a yellow solid powder with a yield of 67%. MS(EI)M + = 329, 1 H NMR (CDCl 3 , 300MHz): δ9.92(s, 3H), 7.84(d, 6H), 7.24(d, 6H).

[0033] (2) Add 0.4g (1.3mmol) of 4-bromo-1-bromomethylnaphthalene, 0.384g (1.4mmol) of triphenylphosphine and 10ml of xyl...

Embodiment 2

[0037] Example 2: Synthesis of 4,4'-bis(4-triphenylaminovinylnaphthyl-1-vinyl)triphenylamine.

[0038](1) Preparation of 1-bromo-4-(1-ethylenetriphenylamine)naphthalene: 4-bromo-1-bromomethylnaphthalene quaternary phosphonium salt (0.3g, 0.53mmol) obtained in step 2 of Example 1 and 4- N,N-Diphenylaminobenzaldehyde (0.08g, 0.3mmol) and sodium hydride (0.042g, 1.75mmol) were added to a 100ml three-necked flask, refluxed at 110°C for 6h, cooled, filtered, and the filtrate was taken, concentrated, petroleum Ether was the eluent and separated by column chromatography to obtain yellow 1-bromo-4-(1-ethylenetriphenylamine)naphthalene (0.064 g) with a yield of 40%. MS(EI)M + =476, elemental analysis (%): Cald. C, 75.63; H, 4.65; N, 2.94. Found.75.04; H, 4.16; N.3.28.

[0039] (2) 4,4'-bis(4-triphenylaminovinylnaphthyl-1-vinyl)triphenylamine preparation: under anhydrous and oxygen-free conditions, 0.253g (0.53mmol) 1-bromo-4- (1-ethylenetriphenylamine) naphthalene, 0.08g (0.27mmol) ...

Embodiment 3

[0042] Example 3: Synthesis of 4,4'-bis(4-triphenylaminovinylnaphthyl-1-vinyl)-N,N-diphenylaminobenzoic acid.

[0043] The synthetic method is similar to Example 2, only need to change N, N-bis(4-styrene) aniline in step 2 into N, N-bis(4-styrene)-4-aminobenzoic acid according to the obtained compound . Yield 21%, MS(MALDI)M + =1132.30. Elemental analysis (%): Cald.C, 88.03; H, 5.43; N, 3.71.Found.88.50; H.5.02; N.3.24.

[0044] The molecular formula of the obtained compound is,

[0045]

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PUM

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Abstract

The invention discloses a triphenylamine-naphthalene multi-branch molecule with double-photon polymerization initiation characteristics. Triphenylamine is taken as an electron donor, and naphthalene nucleus with characteristics of an electron receptor are respectively connected with the 4, 4'-bits of triphenylamine through carbon-carbon double bonds to form the topology of'Y-pn knot' with charge transferability; and then the'Y-pn knot' is taken as a connection center to be conjugately connected with a substituent to form a multi-branch molecule with a greater conjugate system. Therefore, the molecule has a great double-photon absorption cross section. The multi-branch molecule has excellent double-photon polymerization initiation capability for methacrylic acid resin with a low polymerization threshold value and a highly fine microstructure obtained from polymerization. The multi-branch molecule has great application value in the double-photon three-dimensional memory and the micro-processing and fabrication fields of photon crystal.

Description

technical field [0001] The invention relates to a class of triphenylamine-naphthalene multi-branch molecules, which have strong two-photon absorption properties and excellent two-photon polymerization initiation properties for methacrylic resins. Background technique [0002] Two-photon absorption refers to the process of exciting the sample with a light source nearly twice the linear absorption wavelength of the sample under strong light excitation, so that it directly absorbs two photons through a virtual intermediate state and jumps to a high-energy state. The absorption and dispersion of light with a longer wavelength are small, and the light wave has strong penetrating ability, and because the transition probability is proportional to the square of the incident light intensity, under the condition of tight focusing of the laser beam, the excited range of the sample is limited to λ 3 Within the volume, the excitation is highly spatially selective. These characteristics ...

Claims

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Application Information

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IPC IPC(8): C08F2/46C08F220/14
Inventor 王筱梅张唯舟杨平陈庆
Owner SUZHOU UNIV
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