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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[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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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.

Application Domain

Organic compound preparationCarboxylic acid esters preparation +8

Technology Topic

Nonlinear absorptionSolubility +11

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Experimental program(10)

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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Methods and compositions for thermally treating a conduit used for hydrocarbon production or transmission to help remove paraffin wax buildup

InactiveUS20080069961A1Promote meltingImprove solubilityOrganic-compounds/hydrides/coordination-complexes catalystsHollow article cleaningParaffin waxExothermic reaction

Owner:HALLIBURTON ENERGY SERVICES INC

Nanometer miconazole nitrate emulsion medicine and its prepn process

InactiveCN1931164AImprove solubilityImprove bioavailabilityOrganic active ingredientsAntimycoticsPolymer chemistryOil phase

Owner:NORTHWEST A & F UNIV

Classification and recommendation of technical efficacy words

Improve solubility

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

AI-Extracted Technical Summary

Problems solved by technology

Abstract

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Examples

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Example Embodiment

Example Embodiment

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Description & Claims & Application Information

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