Method for improving nonlinear absorption performance of warped acene compound

A technology for nonlinear absorption and benzene compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, preparation of aminohydroxyl compounds, etc., and can solve problems such as the inability to improve the nonlinear absorption performance of twisted acene compounds

Active Publication Date: 2019-04-16
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to solve the existing problem that it is impossible to improve the nonlinear absorption p

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  • Method for improving nonlinear absorption performance of warped acene compound
  • Method for improving nonlinear absorption performance of warped acene compound

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specific Embodiment approach 1

[0007] Specific Embodiment 1: This embodiment is a method for improving the nonlinear absorption performance of twisted acene compounds. The twisted acene compound is a pyrenylacene molecule, and its structural formula is: Improve the ratio of the LUMO orbital occupancy of the three benzene ring structures of the linear pyrenyl acene molecule to the occupancy ratio of the HOMO orbital, that is, the ratio of LUMO / HOMO, and the linear three benzene ring structures of the pyrenyl acene molecule are divided by linear The structure of three benzene rings outside the pyrenyl benzene ring at the end of naphthacene.

[0008] There are large conjugated systems in the molecules of twisted acene compounds, not all conjugated systems in the molecules play a decisive role in the nonlinear absorption performance, such as pyrenyl acene molecules, its optical nonlinear function The center is a linear three benzene ring structure (three benzene ring structures except the pyrenyl benzene ring ...

specific Embodiment approach 2

[0009] Embodiment 2: The difference between this embodiment and Embodiment 1 is that the pyrenyl acene molecule is 2,7-di-tert-butyl-9,17-diphenyl-11-methoxy-12 -((4-fluorophenyl)ethynyl)-dibenzo[de,qr]tetracene, the structural formula of which is: The LUMO orbital occupancy rate is 65%, the HOMO orbital occupancy rate is 56%, and the ratio of LUMO / HOMO is 1.16; the two-photon absorption cross section at the wavelength of 515nm is 561GM. Others are the same as the first embodiment.

[0010] Due to the 2,7-di-tert-butyl-9,17-diphenyl-11-methoxy-12-((4-fluorophenyl)ethynyl)-dibenzo[de,qr obtained in this embodiment ]Tetracene has a two-photon absorption cross section of 561GM at a wavelength of 515nm, so it can be used to prepare optical limiting devices.

specific Embodiment approach 3

[0011] Specific embodiment three: the difference between this embodiment and specific embodiment two is: the 2,7-di-tert-butyl-9,17-diphenyl-11-methoxy-12-((4-fluoro The synthetic method of phenyl) ethynyl)-dibenzo [de, qr] tetracene is as follows:

[0012] Put 2,7-di-tert-butyl-9,17-diphenyl-11-methoxy-12-bromo-dibenzo[de,qr]tetracene into the reactor, add tetrahydrofuran and triethyl amine, then add 4-fluorophenylacetylene, add cuprous iodide, triphenylphosphine and bistriphenylphosphine palladium dichloride under the condition of nitrogen protection, then heat up to 80°C, and react at a temperature of 80°C 22h to 26h, then cooled to room temperature, added saturated brine, and extracted with dichloromethane, collected the organic phase, evaporated to dryness under reduced pressure, separated and purified by silica gel chromatography, the eluent was petroleum ether / dichloromethane mixture, The petroleum ether / dichloromethane mixture is formed by mixing petroleum ether and d...

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Abstract

The invention discloses a method for improving the nonlinear absorption performance of a warped acene compound, belongs to the field of synthesized optical nonlinear materials, and particularly relates to a method for improving the nonlinear absorption performance of the warped acene compound. The invention aims at solving the problem in the prior art that the nonlinear absorption performance of the warped acene compound cannot be improved. According to the method for improving the nonlinear absorption performance of the warped acene compound, the warped acene compound comprises pyrenyl acenemolecules, and the ratio of the LUMO track occupancy to the HOMO track occupancy of three linear benzene ring structures of the pyrenyl acene molecules is increased, that is to say, the ratio of LUMO/HOMO is increased. The method has the advantages that by increasing the ratio of LUMO/HOMO, the biphoton absorption cross section of the pyrenyl acene molecules is enlarged, and the purpose of improving the nonlinear absorption performance of the pyrenyl acene molecules is achieved. The method is mainly used for synthesizing the warped acene compound.

Description

technical field [0001] The invention belongs to the field of synthetic optical nonlinear materials, in particular to a method for improving the nonlinear absorption performance of twisted acene compounds. Background technique [0002] The nonlinearity of organic compounds is the phenomenon that the compound electrons absorb the photon energy of the laser light under the action of the laser light, which leads to the change of its high-order polarizability. Especially the large π-conjugated structure system has attracted extensive attention because of its highly delocalized π-electrons. The structure determines its performance, and the study of the relationship between the structure of its π-conjugated system and the optical nonlinear properties has become the top priority of the current research on organic conjugated nonlinear materials. Pyrenylacene molecules with distorted topology are good optical nonlinear materials because of their very large π-conjugated system and hig...

Claims

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Application Information

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IPC IPC(8): C07C43/225C07C43/215C07C41/30C07C213/02C07C217/78
CPCC07C43/215C07C43/225C07C217/78
Inventor 宋瑛林韩艳兵肖金冲侯红卫张学如王玉晓杨昆石光
Owner HARBIN INST OF TECH
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