Hexylthiophene compound with side chain end capable of being functionalized and preparation method thereof

Abstract

The invention discloses a hexylthiophene compound with a side chain end capable of being functionalized and a preparation method thereof, and belongs to the technical field of organic optoelectronic functional materials. The structure of the compound is shown in the specification, and X is Cl, Br, I, p-methoxyphenoxy, alkylonide silicone epoxy of C1-C6. The compound is synthesized through the method that 2,5-dibromothiophene is adopted as the raw material, an upper hexyl side chain first reacts through Friedel-Crafts acylation, then halogen atom protecting group side chain end functional groups react, carbonyl is restored through a Huang ming-long reaction, and finally protecting groups are removed. In the synthesis path, the raw materials are cheap and easy to obtain, the reaction conditions are easy, the synthesis path is suitable for batch production, products are easy to separate and purify, and a series of hexylthiophene compounds with side chain ends capable of being functionalized can be obtained at the same time. The compound can be used as a synthetic reaction block of multifunctional polymer or macromolecule optoelectronic functional materials.

Description

technical field [0001] The invention belongs to the technical field of organic photoelectric functional materials, in particular to a class of hexylthiophene compounds whose side chain terminals can be functionalized and a preparation method thereof. Background technique [0002] In recent years, since the functionalization of side chains can endow polymers or macromolecular optoelectronic functional materials with excellent properties, the synthesis of organic optoelectronic functional materials based on side chain terminal functionalization has attracted people's attention. This is because the functionalization of this type of material can minimize the impact of the introduction and reaction of functional groups on the photoelectric properties of the material, and can also endow the material with new functions and values. For example: by introducing crosslinking groups, the preparation of multilayer organic photoelectric devices can be realized (U.S. Pat. Appl. Publ. 2015...

AI Technical Summary

Problems solved by technology

This method can obtain high-purity target products, which is beneficial to further reactions to obtain high-molecular-weight polymers or high-purity macromolecular compounds. However, the synthetic route is relatively long, and 1,6-dibromohexane, which is protected at one end, needs to pass through multiple times. The recrystallization of the Grignard reagent can only be obtained, and the concentration of the final Grignard reagent is difficult to measure during the preparation process of the Grignard reagent, and the preparation of the Grignard reagent and the Kumada coupling reaction also require strict anhydrous and oxygen-free operations, which is not easy to achieve

[0003] In summary, the existing hexylthiophene compounds that can be functionalized at the end of the side chain are limited, only 2,5-dibromo-3-bromohexylthiophene, and the synthesis method or reaction conditions are harsh and difficult to purify. Difficult to industrialize

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