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Double-donor organic optical nonlinear chromophore modified by thio-isophorone bridge as well as synthesis method and application of double-donor organic optical nonlinear chromophore

A technology of optical nonlinearity and synthesis method, which is applied in the field of dual-donor organic optical nonlinear chromophore and its synthesis, and can solve the problem that functional groups cannot be further modified.

Pending Publication Date: 2022-06-24
GUANGZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, bis(N,N-diethyl)aniline-based donors have some disadvantages, such as the inability to further modify and introduce other functional groups

Method used

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  • Double-donor organic optical nonlinear chromophore modified by thio-isophorone bridge as well as synthesis method and application of double-donor organic optical nonlinear chromophore
  • Double-donor organic optical nonlinear chromophore modified by thio-isophorone bridge as well as synthesis method and application of double-donor organic optical nonlinear chromophore
  • Double-donor organic optical nonlinear chromophore modified by thio-isophorone bridge as well as synthesis method and application of double-donor organic optical nonlinear chromophore

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Embodiment 1

[0074] A dual-donor organic optical nonlinear chromophore modified by a thioisophorone bridge, the synthesis method comprising the following steps:

[0075] S1. Under N2 atmosphere, diethyl(cyanoethyl)-phosphonate (16.12 mL, 18.22 g, 102.7 mmol) was slowly added to a flask filled with sodium hydride (4.08 g, 102.7 mmol) and 40 mL of dry tetrahydrofuran. Compound (1) (15 g, 25.6 mmol) was then added to THF (90 mL) and refluxed overnight. After removing tetrahydrofuran in vacuo, it was directly purified by silica gel elution column chromatography with ethyl acetate / n-hexane (1:15-1:10) to obtain compound (2) in 70% yield (10.91 g, 17.9 mmol). MS(MALDI)(M+,C 23 H 29 N 3 ):calcd:347.29;found:347.23. 1 H-NMR (400MHz, acetone-d6): d=7.33–7.26 (m, 2H, Ar–H), 7.26–7.17 (m, 2H, Ar–H), 6.78–6.73 (m, 2H, Ar–H) ), 6.72–6.67 (m, 2H, Ar–H), 5.48 (s, 1H, CH), 3.46 (m, 8H, CH) 2 N),1.18(dt,J=10.4,7.0Hz,12H,4Me). 13 C-NMR (100MHz, acetone-d6): d=163.64, 150.23, 149.81, 132.25, 131.17, 1...

Embodiment 2

[0091] A dual-donor organic optical nonlinear chromophore modified by a thioisophorone bridge, the synthesis method comprising the following steps:

[0092] P1, diethyl (cyanomethyl)-phosphonate is slowly added to the tetrahydrofuran solution of sodium hydride, the compound (1) is added, and a reflux reaction is carried out under a protective atmosphere. After the reaction is completed, the solvent is evaporated and passed through Purification by silica gel chromatography, eluting with a mixed solvent of ethyl acetate and hexane, gave compound (2);

[0093] P2. Slowly add the hexane solution of diisobutylaluminum hydride to the toluene solution of the compound (2), react for a period of time at -78°C under a protective atmosphere, add water-containing wet silica gel, and continue at 0°C After the reaction is completed, the product is added to water, extracted with ethyl acetate, purified by silica gel chromatography after concentration, and eluted with a mixed solvent of ethyl...

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Abstract

The invention relates to a thio-isophorone bridge modified double-donor organic optical nonlinear chromophore as well as a synthesis method and application thereof, and six nonlinear optical chromophores Z1-Z6 are designed and synthesized based on a bis (N, N-diethyl) aniline derivative and a thio-isophorone bridge. The invention designs and synthesizes a theoretically driven EO chromophore Z1-Z6 based on a bis (N, N-diethyl) aniline derivative and a thio-isophorone bridge. Particularly, different functional groups such as tert-butyl trimethylsilane, a tert-butyl (methyl) diphenyl silane derivative, 1, 3-bis (trifluoromethyl) benzene and alkylaniline cyanoacetate are used for modifying the bridging part of the chromophore Z2-Z6. And the donor with stronger electron donor capability can generate larger first-grade hyperpolarizability. In addition to relatively high first-order hyperpolarizability, the special structure of the double donors and an isolating group on a chromophore bridge have relatively high spatial effect, so that the material has relatively high polarization efficiency.

Description

technical field [0001] The invention relates to the field of organic optical materials, in particular to a dual-donor organic optical nonlinear chromophore modified by a thioisophorone bridge and a synthesis method and application thereof. Background technique [0002] Driven by next-generation information technologies such as 5G, Internet of Things, virtual reality and artificial intelligence, the broadband wave is sweeping the world. In the past decade, the information capacity has grown exponentially, and the bandwidth and energy consumption of optical communication networks are under enormous pressure. Electro-optical modulator is the core device for realizing photoelectric information conversion, and it is also the key link to break through the two major technical challenges of bandwidth and energy consumption. [0003] Electro-optic materials are an integral part of electro-optic modulators. Early research on nonlinear optical materials focused on inorganic crystalli...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/68C07F7/18G02F1/361H01L51/46H04B10/516H04B10/70
CPCC07D307/68C07F7/1892G02F1/3613G02F1/3611H04B10/70H04B10/516H10K85/653H10K85/40Y02E10/549
Inventor 曾紫莹刘锋钢王家海
Owner GUANGZHOU UNIVERSITY
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