Polyalkoxy substituted 2,3-dicarboxylate triphenylene and its preparation method

Abstract

The invention discloses a polyalkyloxy substituted 2,3-dicarboxylate benzophenanthrene disk-like molecule . The above hexasubstituted benzophenanthrene derivative has certain liquid crystal performances, has an obviously higher liquid crystal range than a hexaalkyloxy substituted benzophenanthrene derivative due to the introduction of an ester group, and can be used as a good liquid crystal material. The invention also discloses a synthetic method of the above compound. The method is characterized in that a benzophenanthrene skeleton is constructed through a multi-step serial reaction of simple and easily available diarylacetylene as a raw material; the reaction does not relate to the separation of an intermediate, and different substituted types of 2,4-dicarboxylate benzophenanthrene disk-like molecules with the side chain number of 4-7 can be synthesized through substrate control; and more importantly, an electron-withdrawing side chain can be easily introduced into a benzophenanthrene molecule through the method, so the structure of the benzophenanthrene compound is enriched.

Description

technical field [0001] The invention relates to a polyalkoxy substituted 2,3-dicarboxylate triphenylene derivative and a preparation method thereof. Background technique [0002] Triphenylene was first isolated from the pyrolysis product of benzene. Mannich synthesized triphenylene for the first time and determined its structure. Triphenylene is a class of polycyclic aromatic hydrocarbons with a planar delocalized 18π-π electron system. When this type of compound undergoes an electrophilic substitution reaction, due to steric hindrance, etc.2, 3, 6, 7, 10, 11 The substitution of the position is more favorable than that of the 1, 4, 5, 8, 9, and 12 positions, so the common triphenylene derivatives are triphenylenes substituted at the 2, 3, 6, 7, 10, and 11 positions. [0003] Early studies have shown that triphenylene compounds have anti-AIDS activity. In addition, triphenylene derivatives are mainly used in optical storage, organic semiconductors, photoconductors, charge tr...

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Problems solved by technology

Including metal-participated biphenyl-benzene oxidative coupling method (J. Chem. Soc., Chem. Commun., 1994, 465) and terphenyl oxidative coupling method (J. Mater. Chem., 2001, 1618) , but the above method has limitations such as substrates requiring specific functional groups and only suitable for electron-donating alkoxy substituents.

However, it is more difficult to introduce electron-withdrawing groups on the triphenylene skeleton. Taking the introduction of carboxylate as an example, the existing method is to oxidize the methyl group directly connected to the triphenanthrene into a carboxyl group, and then esterify it. Preparation (Eur. J. Org. Chem., 2006, 2889), there are disadvantages such as long reaction steps, harsh conditions, and low yield

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