2, 6-di(aryl)-anthraquinone and preparation method thereof

An aromatic group and anthraquinone technology, which is applied in the field of symmetrical anthraquinone derivatives, can solve the problems of easy decomposition, weak photochemical stability, and restrictions on the application of thin films, and achieve good optical stability and thermal stability. Resistant to photodecomposition and long-lasting effect

Inactive Publication Date: 2012-01-25
SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In recent years, there have been many reports on the preparation and synthesis of organic materials with macromolecular conjugated systems {X.Wang, D.M.Nguyen, C.O.Yanez, L.Rodriguez, H.Y.Ahn, M.V.Bondar, and K.D.Belfield, J. Am.Chem.Soc.2010, 132,

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  • 2, 6-di(aryl)-anthraquinone and preparation method thereof
  • 2, 6-di(aryl)-anthraquinone and preparation method thereof
  • 2, 6-di(aryl)-anthraquinone and preparation method thereof

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Example Embodiment

[0023] Example 1:

[0024] The preparation of 2,6-bis(4-methoxystyryl)-anthraquinone comprises the following steps:

[0025] 2,6-Dibromo-anthraquinone (15 g), 4-methoxystyrene (8.6 g), palladium acetate (0.9 g), tri-O-tolylphosphorus (0.7 g,) were mixed under nitrogen protection atmosphere. Under the conditions, it was added into triethylamine solvent, and heated at 75°C for 48 hours. After the reaction was completed, it was cooled to room temperature, distilled under reduced pressure, separated and washed, dried and concentrated. The target product, 2,6-bis(4-methoxystyryl)-anthraquinone, was obtained by chromatographic column separation, 11.8 g, and the yield was 73%.

Example Embodiment

[0026] Example 2:

[0027] Synthesis of 2,6-bis(4-aminostyryl)-anthraquinone

[0028] 2,6-Dibromo-anthraquinone (15 g), 4-aminostyrene (9.2 g), palladium acetate (1.2 g), tri-O-tolylphosphorus (0.7 g) were prepared under nitrogen protection atmosphere, It was added to triethylamine and heated at 90°C with stirring for 48 hours. After the reaction was completed, it was cooled to room temperature, distilled under reduced pressure, separated and washed, dried and concentrated. The target product, 2,6-bis(4-aminostyryl)-anthraquinone, was obtained by chromatographic column separation, 13.3 g, and the yield was 76%.

Example Embodiment

[0029] Example 3:

[0030] Synthesis of 2,6-bis(4-chlorostyryl)-anthraquinone

[0031] 2,6-dibromo-anthraquinone (15 g), 4-chlorostyrene (9.4 g), palladium acetate (1 g), tri-O-tolylphosphorus (0.7 g) were prepared under nitrogen protection atmosphere, It was added to triethylamine and heated at 90°C with stirring for 24 hours. After the reaction was completed, it was cooled to room temperature, distilled under reduced pressure, separated and washed, dried and concentrated. The target product, 2,6-bis(4-chlorostyryl)-anthraquinone, was obtained by chromatographic column separation, 9.4 g, and the yield was 65%.

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Abstract

The invention relates to 2, 6-di(aryl)-anthraquinone and a preparation method thereof, the preparation method comprises the following steps: connecting electron donor or electron acceptor groups to the two sides of an anthraquinone ring in the 2 and 6 positions, and enabling a 2, 6-dibromo anthraquinone type derivative and a substituent group containing a vinyl group to generate an Heck reaction in alkaline conditions under the catalytic action of palladium acetate and tri-O-methoxy phosphorus for generating the 2, 6-di(aryl)-anthraquinone, and the general formula of the molecular structure of the 2, 6-di(aryl)-anthraquinone is shown in the specification, wherein R is the substituent group containing the vinyl group, the electron donor group or the electron acceptor group. As the compound has the larger conjugate plane and simultaneously has better photochemical stability, thermal stability and solubility, the compound can better capture multiple photons and excite the generation of multi-photon absorption and nonlinear absorption phenomena, and further meet the application requirements in the aspects of photoelectric conversion materials, nonlinear absorption materials and the like.

Description

technical field [0001] The invention relates to a class of symmetrical anthraquinone derivatives, especially a 2,6-bis(aryl)-anthraquinone and a preparation method thereof, which can meet various application requirements of photoelectric conversion materials and nonlinear absorption materials, etc. . Background technique [0002] In recent years, due to the huge application of organic multiphoton absorbing materials in photonics and biomedicine, many scientists have designed new organic molecules with large molecular conjugated systems for them. As early as 1931, Mayer theoretically predicted the existence of this nonlinear phenomenon {see references: [1]P.N.Prasad, D.R.Ulrich, Nonlinear Optical and Electroactive Polymers[M].NewYork, Plenum, 1988.}, and with the development of science and technology The phenomenon of multi-photon absorption has also been discovered and confirmed one by one by scientists in the experimental process {see reference [2]: W.Kaiser, C.G.B.Garr...

Claims

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Application Information

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IPC IPC(8): C07C50/34H01L51/46C07C221/00C07C46/00C07C225/24C09K11/06C07C69/16G02F1/361C07C67/293C07C51/373C07C65/38C07D213/50C07C50/24C07D209/86
CPCY02E10/549
Inventor 李亮吴谊群耿永友
Owner SHANGHAI INST OF OPTICS & FINE MECHANICS CHINESE ACAD OF SCI
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