Highly condensed ring [6]helicene compounds based on fluorene and naphthalene and synthetic method thereof

Abstract

The invention provides a kind of highly condensed ring [6]helicene compounds (I) based on fluorene and naphthalene and synthetic method thereof, and belongs to the technical field of chemical engineering. The highly condensed ring [6]helicene compounds with photoelectric functions are successfully prepared by taking naphthalene and fluorene derivatives as raw materials and employing a photocatalytic cyclization method. The synthetic method has the advantages of high yield, short time, simple operation and the like, also employs common cheap reagents, helps to reduce preparation cost, and is easy for popularization and application. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene has extremely good solubility in different organic solvents, and are beneficial for purification and film making. Multiple highly condensed ring [6]helicene compounds can be obtained by introducing different substitutes. The highly condensed ring [6]helicene compounds based on fluorene and naphthalene is hopeful to be widely applied to fields such as organic electroluminescence, Organic field effect transistor, organic second-order nonlinear or chiral liquid crystal, biological medicines and the like.

Description

technical field [0001] The invention relates to a class of high-condensed ring [6] helicene compounds based on fluorene and naphthalene and a synthesis method thereof, mainly relates to the preparation of [6] helicene compounds by photocatalytic ring-closing reaction method, and belongs to the technical field of chemical industry. Background technique [0002] Helicene is a class of polycyclic aromatic compounds with a helical structure formed by the ortho-condensation of multiple aromatic rings. There are twisted planes in the helicene molecule, which is a typical chiral racemic compound. Fluorene is a kind of promising blue light-emitting chromophore. There are multiple substitutable groups on the structure, such as 2 and 7 positions are easy to undergo electrophilic substitution reaction, and 9 position is easy to undergo alkylation substitution; thus it is easy to introduce functional groups. So far, there have been no reports of helicene compounds containing fluorene ...

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Problems solved by technology

However, the synthesis of many helicene compounds takes a long time and the yield is low, and with the increase of the conjugated system, the helicene with a rigid structure has stronger intermolecular interactions, resulting in poor solubility. For related reports, see L.Liu, et al.J.Org.Chem.1991,56,3769.; F.B.Mallory, et al.J.Am.Chem.Soc.1997,119,2119. In addition, the lack of active sites for the introduction of functional groups It is also a very serious problem in the synthesis of helicene derivatives

There is no report on this type of helicene compound and its synthesis

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