Fused heterocyclic compound and its preparation method

Abstract

The invention discloses a fused-heterocycle compound and a preparation method thereof. A structural general formula is shown as formula 1, X is selected from S or Se; Y is selected from one of S, Se or O; R1 and R2 are selected from hydrogen or iodine, and R1 and R2 are different; R3 is selected from any one of -OH, -OR4 or a polyether group, wherein R4 is an alkyl of a straight chain or a branched chain of C1-C30 or an alkyl of a straight chain or a branched chain of C1-C30 which is substituted by halogen. A series of reactions and hydrolysis are carried out in order to obtain the compound, and at the same time, an intermediate shown in a formula 2 and a preparation method thereof are provided. The preparation method is simple, raw materials have wide sources, products of each reaction have high yields, and obtained yields of target products are higher; the compound shown in the formula 1 can be applied to synthesis of a semi-conducting polymer, and can be used as parent compounds for synthesis of other fused-heterocycle compounds. Structural modification can be carried out in a plurality of modes for the middle shown in the formula 2, so that derivatives with a plurality of structures are obtained.

Description

technical field [0001] The invention belongs to the technical field of preparation of fused heterocyclic compounds, and in particular relates to a condensed heterocyclic compound and a preparation method thereof. Background technique [0002] Fused thiophene derivatives have many beneficial properties. For example, fused thiophene derivatives and their polymers show good electrical conductivity and nonlinear optical properties, which have attracted the attention of researchers. Therefore, since the first case of thienothiophene in 1886 Since the compound was synthesized, researchers have conducted extensive research on the synthesis strategies of thienothiophene derivatives and their polymers, and proposed many synthetic routes. [0003] D.J.Zwanenburg et al. (J.Org.Chem., v31:3363-3365,1966) synthesized 4,6-dihydrothieno[3,4-b]thiophene and its derivatives, wherein R is CH 3 or H. The disadvantages of this method are: (1) the synthesized compound is a hydrogenated thienot...

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Problems solved by technology

The disadvantages of this method are: (1) the synthesized compound is a hydrogenated thienothiophene type compound, which needs further reaction to be converted into a thienothiophene type compound, which obviously prolongs the synthetic route, increases the complexity of operation, and reduces the final The yield of product; (2) used raw material price is higher, has increased synthesis cost

[0004] Yan Yao et al. (Advanced Materials, 19:3979-3983, 2007) also synthesized thieno[3,4-b]thiophene. However, this method was used for bromination, and only two bromines on the thiophene ring could be isolated. Atomic product, such subsequent further structural modification, if only one side needs to be modified, the bromine atom on the other side needs to be replaced

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