Fullerene-perylene functional molecule and preparation method thereof

Abstract

The invention discloses a fullerene-perylene functional molecule and a preparation method thereof, and relates to the technical field of design and synthesis of functional organic molecules. In a structural general formula, two fullerene pyrrole ring compounds with the same structure are symmetrically connected on two anhydrides of perylene dianhydride by a rigid benzidine structure, benzidine is positioned at an axial position of a fullerene pyrrole ring structure, and thus a rigid linear molecule is formed. Firstly, one amino group of benzidine is protected by BOC, BOC protected benzidine is generated and then undergoes a reaction with bromine alkyl acetate, and the product is subjected to a Prato reaction with C60 and glyoxylic acid alkyl ester to synthesize a BOC protected fullerene N-hetero five-membered ring compound, followed by, a BOC protecting group is removed to generate a fullerene N-hetero five-membered ring compound containing an amino active group, and finally the fullerene N-hetero five-membered ring compound is subjected to an amidation reaction with perylene dianhydride to synthesize the functional molecule. The functional molecule can be applied in the fields of organic solar cells, photodynamic therapy and tribology.

Description

technical field [0001] The invention relates to the technical field of design and synthesis of functional organic molecules, in particular to a fullerene-perylene functional molecule and a preparation method thereof. Background technique [0002] Since fullerenes were discovered (Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. Nature 1985, 318, 162.) and successfully isolated ( W.; Lamb, L.D.; Fostiropoulos, K.; Huffman, D.R. Nature 1990, 347, 354.), it has attracted more and more scientists' attention. due to C 60 Special geometric configuration, it exhibits many special properties, such as superconductivity, magnetism, lubrication, electrical, electrochemical and optical properties, etc. Fullerene compounds can also be used in light-promoted DNA cleavage, enzyme inhibitors, and cytotoxicity experiments. But since C 60 The absorption in the visible region is very weak, and only a very weak absorption occurs at 700nm, thus limiting its application in ...

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However, due to the good planarity of this type of molecules, there is a relatively strong π-πstacki

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