8-hexyl-thieno-[3',2':3,4] benzo[1,2-c] carbazole compound and synthesizing method thereof

Abstract

The present invention relates to a 8-hexyl-thieno-[3',2':3,4] benzo[1,2-c] carbazole compound and a synthesizing method thereof. The 8-hexyl-thieno-[3',2':3,4] benzo[1,2-c] carbazole compound with high solubility is prepared from carbazole derivatives and thiophene derivatives which are used as raw materials by using a method of photocatalysis loop closing. The synthesizing method is simple in reaction operation and post-processing and easy in popularization and application. The 8-hexyl-thieno-[3',2':3,4] benzo[1,2-c] carbazole compound can be widely applied in the fields of organic electroluminescence, organic field-effect transistors, organic second-order nonlinerity, chiral liquid crystals, biological medicines and the like.

Description

technical field [0001] The present invention specifically relates to a class of 8-hexyl-thieno[3',2'3,4]benzo[1,2-c]carbazole compounds (belonging to thiaza[5]helicene compounds) and their synthesis The method belongs to the technical field of organic synthesis. Background technique [0002] Helicene compounds, especially heteroatom helicene compounds and their synthesis methods are currently a research hotspot in the field of organic synthesis. The research progress of heteroatom [5] helicene compounds in recent years is as follows: Caronna synthesized bis-aza [5] helicene from symmetrical stilbene, see Bazzini, C.; Brovelli, S.; Caronna, T., etal.Eur.J.Org.Chem.2005,1247-1257; Abbate synthesized 1-aza and / or 3- Aza[5]helicene, see Abbate, S.; Bazzini, C.; Caronna, T., etal.Tetrahedron, 2006,62,139-148); Adam with 2,9-dimethyl-1,10-phenanthrene Hexaaza[5]helicene was synthesized from roline, see Adam, R.; Ballesteros-Garrido, R.; Vallcorba, O., et al. Tetrahedron Lett. 2...

AI Technical Summary

Problems solved by technology

Tanaka's metal-mediated biaryl coupling reaction using TiCl 3 , DME and Zn-Cu complex synthesized [7] helicene, see Tanaka, K., et al., J.Org.Chem.1997,62,4465-4470), but this method is more complicated, and the reaction time Long, took nearly 40 hours

Ogawa according to the oxy-Cope rearrangement reaction, using KH, 18-crown ether-6, THF, NaBH 4 , EtOH, etc. have synthesized 2-acetoxy[5]helicene, see Ogawa, Y., et al., Tetrahedron Lett.2002, 43, 7827–7829, but it is still difficult to use this method from the ring-closing precursor to the final helicene Need to go through 6 steps of reaction, too many reaction steps, more cumbersome

Shawn synthesized a series of helicenes based on olefin displacement using microwave heating technology, sealed tubes, dichloromethane and ruthenium catalysts, see hawn, K.C., et al., Angew.Chem.Int.Ed.2006,45,2923- 2926, but this method requires relatively high reaction conditions, and the catalyst used is more expensive, resulting in higher synthesis costs

Ichikawa synthesized a series of helicenes using magic acid, hexafluoroisopropanol, carbon triphenyltetrafluoroborate and 1,2-dichloroethane according to the Fuckers-type cyclization, see Ichikawa, J., et al .,Angew.Chem.Int.Ed.2008,47,4870-4873, but this method is cumbersome. It needs 3 steps from the ring-closing precursor to the final helicene, and the reagents required for the reaction are relatively expensive

Oyama synthesized dimethylsilyl[7]helicene using platinum chloride and 1,2-dichloroethane, see Oyama, H., et al., Org. Lett.2013, 15(9), 2104-2107 , but the platinum chloride catalyst used in this method is relatively expensive

Ruch synthesized a series of helicenes using benzylamine, palladium acetate, 4,5-bisdiphenylphosphine-9,9-dimethylxanthene and cesium carbonate, see Ruch, A.A., Org. Biomol. Chem. 2016,14,8123–8140, but this method is cumbersome and has many by-products

To sum up, many of these routes and synthetic methods have disadvantages such as complex synthesis of raw materials, many reaction steps, long reaction time, high cost, cumbersome operation and post-processing, etc., and their practical and economic value are greatly limited.

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