A method for improving nonlinear absorption properties of twisted acene compounds

A technology for nonlinear absorption and benzene compounds, which is applied in the preparation of organic compounds, chemical instruments and methods, and the preparation of aminohydroxyl compounds. The effect of absorbing properties

Active Publication Date: 2021-12-10
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 performance of twisted acene compounds, and provide a method for improving the nonlinear absorption performance of twisted acene compounds

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  • A method for improving nonlinear absorption properties of twisted acene compounds
  • A method for improving nonlinear absorption properties of twisted acene compounds

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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

A method for improving the nonlinear absorption performance of twisted acene compounds belongs to the field of synthetic optical nonlinear materials, and in particular relates to a method for improving the nonlinear absorption performance of twisted acene compounds. The purpose of the present invention is to solve the existing problem that the non-linear absorption performance of twisted acene compounds cannot be improved. A method for improving the nonlinear absorption performance of a twisted acene compound, the twisted acene compound being a pyrenyl acene molecule; improving the LUMO orbital occupancy and the HOMO orbital occupancy of the three benzene ring structures of the pyrenyl acene molecule linear Rate ratio, that is, the ratio of LUMO / HOMO. Beneficial effects: by increasing the ratio of LUMO / HOMO, the two-photon absorption cross section of the pyrenylacene molecule is further improved, and the purpose of improving the nonlinear absorption performance of the pyrenylacene molecule is realized. The invention is mainly used for preparing and synthesizing twisted acene compounds.

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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Patent Type & Authority Patents(China)
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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