CN-122010897-A - Naphthiophene compound, preparation method and application

Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a naphthothiophene compound, a preparation method and application thereof. According to the invention, naphthalene thioglycoland alpha-bromocinnamaldehyde are used as raw materials under the condition of no light catalyst and additive, and the naphthothiophene compound is prepared at room temperature in an air atmosphere. Compared with the preparation method reported previously, the method has the advantages of green, environment protection, safety, high efficiency and energy conservation, the application range of the substrate is wide, the compatibility of the functional groups of the product is good, transition metal, photocatalyst and external oxidant are not needed, and the method can be used for simply and conveniently synthesizing the organic photoelectric material.

Inventors

• CHEN ZIREN
• LIU CHENJIANG
• GUO TONG

Assignees

• 新疆大学

Dates

Publication Date

20260512

Application Date

20260129

Claims (8)

1. 1. A naphthothiophene compound is characterized in that, the structural formula of the naphthothiophene compound is as follows: ; Wherein R 1 is hydrogen, alkyl, fluorine, chlorine, bromine and trifluoromethyl, R 2 is hydrogen, p-bromo-substituted phenyl, p-nitro-substituted phenyl, m-bromo-substituted phenyl and 2, 3-dichloro-substituted phenyl.
2. 2. A process for the preparation of naphthothiophenes according to claim 1, wherein, ; R 1 -R 2 is as defined in claim 1.
3. 3. The method for producing a naphthothiophene compound according to claim 2, wherein naphthalene thiol is used as a raw material, cesium carbonate is used as a base, and the reaction is carried out with α -bromocinnamaldehyde under the irradiation of visible light to produce the naphthothiophene compound.
4. 4. The method for preparing naphthothiophene compounds according to claim 3, wherein the molar ratio of naphthalene thiol, α -bromocinnamaldehyde and cesium carbonate is 1:2:1-2:1:1.
5. 5. The method for producing a naphthothiophene compound according to claim 3, wherein the visible light is irradiated under one or more light sources selected from the group consisting of 5000-5500K white light, 395-400 nm violet light, 455-460 nm blue light, and the power of the irradiation light source is 6-10W.
6. 6. The process for producing a naphthothiophene compound according to claim 3, wherein the reaction time is 24 to 30 hours, the reaction temperature is room temperature, and the reaction atmosphere is an air atmosphere.
7. 7. The method for producing a naphthothiophene compound according to claim 3, wherein the reaction solvent is one or more of ethyl acetate and methanol.
8. 8. Use of the naphthothiophene compound according to claim 1 or the naphthothiophene compound prepared by the methods according to claims 2 and 3 in organic photoelectric materials.

Description

Naphthiophene compound, preparation method and application Technical Field The invention belongs to the technical field of organic synthesis, and particularly relates to a naphthothiophene compound, a preparation method and application thereof. Background The naphthothiophene condensed ring compound (mainly comprising condensed structures such as naphtho [2,1-b ] thiophene, naphtho [1,2-b ] thiophene and the like) is paid attention to due to the unique structure and property, and has wide application prospect in the field of organic photoelectric materials. However, conventional synthetic methods for their backbones still face a number of challenges. The existing strategies mostly rely on transition metal catalysis and heating conditions and usually require the help of stoichiometric oxidants to complete the critical steps, which not only do not conform to the concept of green chemistry, but also limit its scope of application. In recent years, with the development of visible light catalytic technology, photo-redox catalysis has been widely used for the construction of thiophene rings. However, synthesis of naphthothiophene compounds is realized through an electron donor-acceptor (EDA) complex pathway under the induction of visible light, and has not been reported in the literature at present. Therefore, developing a green method for preparing naphthothiophene compounds by cyclization of naphthalene thiol and alpha-bromocinnamaldehyde directly in a mild neutral system without adding a photocatalyst and a metal catalyst under the condition of visible light has become a technical challenge to be solved in the field. Disclosure of Invention In order to solve the problem, the invention discloses a naphthothiophene compound, a preparation method and application thereof. The invention provides a simple, green and easy-to-amplify synthesis method, which takes naphthalene thiol and alpha-bromocinnamaldehyde as raw materials, and can synthesize a series of naphthothiophene compounds under the condition of visible light irradiation and room temperature. The method has the advantages of simple and convenient operation, mild conditions, no need of depending on transition metal catalysts, external photosensitizers or other additives, smooth operation in air, and good atomic economy and step simplicity. By using the method, naphthothiophene derivatives with various structures can be quickly constructed to synthesize the organic photoelectric material. In order to achieve the above purpose, the present invention adopts the following technical scheme: The first technical purpose of the invention is to provide a naphthothiophene compound, wherein the naphthothiophene compound has the following structure: ; Wherein R 1 is hydrogen, alkyl, fluorine, chlorine, bromine and trifluoromethyl, R 2 is hydrogen, p-bromo-substituted phenyl, p-nitro-substituted phenyl, m-bromo-substituted phenyl and 2, 3-dichloro-substituted phenyl. The second technical purpose of the invention is to provide a preparation method of the naphthothiophene compound, which comprises the following synthetic route: ; R 1 and R 2 are as defined above. Specifically, naphthalene mercaptan is used as a raw material, cesium carbonate is used as alkali, and the naphthalene mercaptan reacts with alpha-bromocinnamaldehyde under the irradiation condition of visible light to generate a naphthothiophene compound. Optionally, the molar ratio of naphthalene thiol, alpha-bromocinnamaldehyde and cesium carbonate is 1:2:1-2:1:1. Optionally, the visible light irradiates under one or more than two light sources selected from 5000-5500K white light, 395-400 nm purple light and 460-465 nm blue light, and the power of the irradiation light source is 6-10W, specifically one of 6W, 8W and 10W. Alternatively, the reaction time is 24-30 hours, the reaction temperature is room temperature, and the reaction atmosphere is air atmosphere. Optionally, the reaction solvent is one or more of ethyl acetate and methanol. Further, in the method, after the reaction is finished, the product is separated and characterized according to a conventional separation and purification method, and the corresponding product is obtained. The third technical aim of the invention is to provide an application of the naphthothiophene compound in organic photoelectric materials. Furthermore, the naphthothiophene compound can be used as an organic photoelectric material. It should be noted that, the naphthothiophene condensed ring compound (mainly including naphtho [2,1-b ] thiophene, naphtho [1,2-b ] thiophene and other structures) has wide application prospect in the field of organic photoelectric materials. The compounds are commonly used as fluorescent dyes, molecular probes and photoelectric functional materials, and show excellent photophysical properties and charge transport characteristics. Based on the above, the naphthothiophene compound synthesized/prepared by the method has application value in the fi