Synthetic method of V-type rigid-flexible molecule based on pyrene and multi-branch polyethylene glycol chains

Abstract

The invention discloses a synthetic method of a V-type rigid-flexible molecule based on pyrene and multi-branch polyethylene glycol chains, and the structural general formula of the compound is as shown in the specification. The preparation method comprises the following specific steps: refluxing a compound having the structure formula as show in the specification, another compound having the structure formula as show in the specification and anhydrous sodium carbonate in a solvent to react to obtain a compound having the structure formula as show in the specification, refluxing the compound in the presence of potassium hydroxide, adding concentrated hydrochloric acid for acidification, so as to obtain a compound having the structure formula as show in the specification; dissolving the obtained compound and dimethylformamide in a solvent, allowing the compound to react with thionyl chloride to obtain a compound having the structure formula as show in the specification, refluxing the obtained compound and 4-hydroxyl-4'-iodo-biphenyl to react, carrying out a sonogashira reaction on the obtained compound and a compound having the structure formula as show in the specification, so as to obtain the V-type rigid-flexible molecule based on pyrene and multi-branch polyethylene glycol chains. The method has the advantages of being reasonable in synthesis process and high in yield, the product has stronger fluorescence in an organic solvent and can be used as a fluorescent dye or a fluorescent molecular probe; and has good self-assembly performance in an aqueous solution; the structured aggregate can be used as a nano reactor or a drug carrier.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and relates to a method for synthesizing a V-shaped rigid and flexible molecule, in particular to a method for synthesizing a V-shaped rigid and flexible molecule based on pyrene and multi-branched polyethylene glycol chains. Background technique [0002] In recent years, the design and synthesis of new building elements with self-assembly capabilities, the development of assembly methods based on various driving forces, and the construction of supramolecular systems with different physical and chemical properties are the research hotspots of supramolecular science. At present, systems such as block copolymers, rigid and flexible molecules, liquid crystals, and peptide complexes can self-assemble into supramolecular aggregates with perfect shapes and sizes. In these artificially synthesized self-assembled systems, rigid and flexible molecules can self-assemble into a variety of supramolecular nanostru...

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Problems solved by technology

[0004] At present, rigid and flexible molecules based on the V-type rigid block of the benzene ring have been reported (H-J Kim; Y-H Jeong; E Lee et al.J.Am.Chem.Soc.,2009,131(47):17371-17375; L Liu; H-J Kim; M Lee.SoftMatter,2011,7(1):91-95;H J Kim;S K Kang;Y K Lee et al.Angew.Chem.Int.Ed.,2010,49(45):8471- 8475; H J Kim; F Liu; J H Ryu et al.J.Am.Chem.Soc.,2012,134(33):13871-13880; Z Huang; S K Kang; M Banno et al.Science,2012,337( 6101):1521-1526; S Shin; S Lim; Y Kim et al.J.Am.Chem.Soc.,2013,135(6):2156-2159; H-J Kim; J-K Kim; M Lee.Chem.Commun ., 2010,46(9):1458-1460), but these molecules are all substituted benzenes as the core to construct a V-shaped rigid block, and introduce a single flexible chain on the side of the rigid block. There are many changes, but the influence of the flexible chain connection position and the number of flexible chains on the self-assembly behavior of V-type rigid-flexible molecules is not yet clear; Other physical properties, etc., are subject to further in-depth research.

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