Synthesis method of indenofluorene derivatives, isotruxene and mono-substituted isotruxene derivatives

Abstract

The invention discloses a synthesis method of indenofluorene derivatives, isotruxene and mono-substituted isotruxene derivatives. The synthesis method of indenofluorene derivatives is characterized in that ester-group-containing compounds are formed through Diels-Alder reaction of methyl propiolate and indenocyclopentadienone, ethyl substituted indenofluorene derivatives are formed through hydrolysis, acid catalytic ring closing, carbonyl reduction and introduction of ethyl onto methylene, diketone compounds produced after ring closing react with lithium salt of 4, 4'-di-tert-butyl-2-brominated biphenyl, and then acidification and ring closing are conducted to obtain indenofluorene derivatives with spirofluorene. The synthesis method of isotruxene is characterized in that 1, 4-diphenyl-2, 3-di (carbalkoxy) fluorenone products are formed through the Diels-Alder reaction of indenocyclopentadienone and dimethyl acetylenedicarboxylate, isotruxene ketone is obtained through hydrolysis and acid catalytic ring closing and finally isotruxene is obtained; dibenzyl alcohol products are formed through the Diels-Alder reaction of 1, 4-butynediol and indenocyclopentadienone, and isotruxene is obtained through acetone protection, carbonyl reduction, acetone removal and polyphosphoric acid (PPA) ring closing; and oriented oxy substituted products, i.e. isotruxene ketone which is derived from isotruxene with methylene at a No.5 position being substituted, and corresponding diethyl substituted products are additionally obtained. The indenofluorene derivatives, the isotruxene and the mono-substituted isotruxene derivatives disclosed by the invention can be used in the field of organic electroluminescence and organic micro-molecule solar cells.

Description

technical field [0001] The invention belongs to the technical field of organic electroluminescent materials and organic small molecule solar cells, and specifically relates to a novel synthesis method of a class of indenofluorene derivatives, isotriindene derivatives, and the synthesis of novel monosubstituted isotriindene derivatives. Specifically, indene [2,1- c ] and fluorene and indene [1,2- a ] and fluorene as the parent, through a series of conventional synthesis methods, introducing ethyl groups and spirofluorene structures to form a series of indenofluorene and spirofluorene derivatives; from isotriindanone or 1,4-diphenyl- 2,3-bis(hydroxymethyl)fluorene to produce isotripolyindene; from 1,4-diphenyl-2,3-bis(hydroxymethyl)-9,9-diethylfluorene and 1,4 -Diphenyl-2,3-bis(chloromethyl)-9-fluorenone was used to obtain 5,5-diethylisotriindene and 5-oxoisotriindene respectively. Background technique [0002] Indenofluorene (Indenofluorene, IF) has five isomers, that is, ...

AI Technical Summary

Problems solved by technology

The reason is that the traditional synthetic method has tedious and harsh conditions and the yield is very low, which limits its research and development.

In 2006, the Yang Jishui research group of National Taiwan University reported an improved method for synthesizing isotrisindene: using indene as a structural unit, cyclotrimerization under certain conditions produces isotrisindene, but the yield is only 18%, and the reaction was blocked. Limited to trace levels (10mmol) (J.-S. Yang, Y.-R. Lee, J.-L. Yan, M.-C. Lu. Org. Lett., 2006, 8, 5813)

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