A class of macrocyclic and cage-like molecules and derivatives based on biphenyl aromatic hydrocarbons and their synthesis methods and applications

Abstract

The invention discloses a class of macrocyclic and cage-like molecules and derivative compounds based on biphenyl aromatic hydrocarbons and a synthesis method and application thereof. It mainly converts bis-(2,4-dialkoxyphenyl) aromatics (naphthalene, anthracene, pyrene, porphyrin, etc.) or tris-(2,4-dialkoxyphenyl) aromatics (benzene, all Tribenzone) and paraformaldehyde were catalyzed by Lewis acids to obtain a series of new macrocycles in high yields. In addition, demethylation can obtain perhydroxybiphenyl aromatics (tetrabiphenyl trimerization, naphthalene dimerization, etc.), and further modification can obtain a variety of water-soluble derivatives, showing good bonds to guest molecules (viologen, etc.) combined ability. Moreover, the functional groups introduced into the skeleton make the biphenyl aromatics have excellent adsorption and separation ability and photophysical properties. The advantages of the present invention are: the raw materials of biphenyl aromatic hydrocarbons can be purchased commercially, the synthesis is simple, the yield is high, and the modification is convenient, so that it has a wide range of gas adsorption and separation, performance improvement of luminescent materials, and adsorption of water-soluble toxic substances. application prospects.

Description

technical field [0001] The invention belongs to the synthesis and derivatization of supramolecular macrocycles and molecular cages, in particular to a class of macrocycles and cage-like molecules and derivative compounds based on biphenyl aromatic hydrocarbons and a synthesis method and application thereof. Background technique [0002] Since the discovery of the first generation of macrocyclic host crown ethers, macrocyclic molecules have been shown to be essential for recognition and assembly, and thus have broad applications in chemistry, materials, and biology. Their wide range of applications makes the synthesis of new macrocycles extremely attractive. Chemists have put a lot of effort into synthesizing macrocyclic compounds such as Texas Ring, ExBox, Pillar Arene, Bamboo Urea, Pillar Complex, Cycloparaphenylene, Caliximidazole, Calixpyrrole, Cyanostar, etc. . However, their modifications are mainly limited to edge or side chain moieties, and any changes in the backbo...

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Problems solved by technology

[0003] The purpose of the present invention is to provide a simple, efficient and general method for synthesizing biphenyl arene macrocycles and molecular cages for the problems of cumbersome synthesis routes, low yields and few modification sites, and to develop further derivatization methods. Methods

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