Method for synthesizing pyrene-4,5,9,10-tetralone

Abstract

The invention discloses a method for synthesizing pyrene-4,5,9,10-tetralone. The method includes the steps: (1) performing coupling reaction of 2,6-dioctyl phthalate methyl ester-1-bromobenzene and copper powder in organic solvents N and N-dimethylformamide to synthesize 2,2',6,6'-tetramethyl methyl formate biphenyl; (2) refluxing the 2,2',6,6'-tetramethyl methyl formate biphenyl and metal sodium in toluene for 2-4 hours in nitrogen atmosphere, cooling the 2,2',6,6'-tetramethyl methyl formate biphenyl and the metal sodium, washing the 2,2',6,6'-tetramethyl methyl formate biphenyl and the metal sodium after removing sodium blocks, combining organic phases and adding ethanol to ensure complete consumption of the metal sodium; and adding acid for acidizing, adding double salicylamide ethyl cobalt and methanol and performing reaction in oxygen atmosphere to obtain the pyrene-4,5,9,10-tetralone. The method has the advantages that 1) used reagents are low in cost and wide in source; 2) the synthesis process is reliable and conditions are moderate; and 3) the conversion rate of all reaction is extremely high, and products are easily purified.

Description

technical field [0001] The invention belongs to fine chemical products, in particular to a method for synthesizing pyrene-4,5,9,10-tetraketone (pyrene tetraketone). Background technique [0002] Pyrene-4,5,9,10-tetraketone, also referred to as pyrenetetraone, is an important fine chemical product and an important raw material and intermediate for the synthesis of pyrene derivatives and other fused ring compounds. For example, reacting with pyrene-4,5,9,10-tetraketone as raw material and o-phenylenediamine, etc., can obtain soluble graphite nanoribbons (nano-ribbon) ((a) Wasserfallen, D.; Kastler, M.; Pisula, W.; Hofer, W.A.; Fogel, Y.; Wang, Z.H.; .; Andrienko, D.; Rader, H.J.; Mullen, K.Macromolecules 2009, 42, 6878.), due to the conjugation characteristics of this kind of material structure, it can transport charge, stimulate light, and thus can or may be in many It has been applied in electronic or optoelectronic devices, such as polymer light-emitting diodes, photovolt...

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Problems solved by technology

[0003] At present, there are three main methods for synthesizing pyrene-4,5,9,10-tetraketone (see figure 1 ): 1) use ruthenium trichloride to catalyze the oxidation of pyrene with sodium periodate (Hu, J.; Zhang, D.; Harris, F.W.J.Org.Chem.2005, 70, 707.), the route is characterized by steps Short, but expensive precious metal ruthenium must be used, and the yield is only 35%; 2) Synthesize pyrene-4,5-dione first, and then oxidize with oxidants such as chromium trioxide (Stille, J.K.; Mainen, E.L.Macromolecules 1968, 1, 36.), this route is because of stepwise reaction, productive rate is very low, only 15%, almost nobody adopts at present; 3) oxidation pyrene-4,5,9,10-tetraphenols prepare (Wasserfallen, D.; , M.; Pisula, W.; Hofer, W.A.; Fogel, Y.; Wang, Z.H.; Mullen, K.J.Am.Chem.Soc.2006, 128, 1334.), although the single-step yield of this route is higher (65 %), but the preparation of raw materials is quite difficult and does not have production value

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