Study On Synthesis And Properties Of Novel Benzo-15-crown-5-based Organic Fluorescent Compounds

The synthesis of benzocrown ether-type fluorescent compounds is one of the most popular topics in supramolecular chemistry nowadays.The benzocrown ether plays an important role in obtaining novel structures and performances due to the abundance and flexibility of the combination with the organic group.In this study,eight novel benzocrown ether compounds were designed and synthesized using 4-substituted benzo-15-crown-5 as matrix by adding fluorescent groups,and their fluorescence properties were systematically studied by introducing fluorophores.1,The synthesis process conditions of the key intermediate 4-aldehyde benzo-15-crown-5 were optimized,and a Schiff base compound（TPE-a）that can specifically recognize Bi³⁺was synthesized by 4-aldehyde benzo-15-crown-5 reaction with 1-amino-4-（1,2,2-Tribenzoyl）benzene.The detection limit for Bi³⁺was 0.33 n M.The compound has high selectivity and good sensitivity,which provides a new method for the detection of Bi³⁺.2,A new method for the synthesis of 4-benzoyl benzocrown ether was proposed,and the symmetrical tetrastyrene bis crown ether compound（TPE-b）was synthesized by classical Mc Murry reaction.Compared with compound TPE-a,it was confirmed that the existence of tetrastyrene makes the compound have AIE properties,and the compact arrangement of molecules will affect the fluorescence properties of the compound.3,Two benzocrown ether Schiff base compounds（NBC-1 and NBC-2）containing naphthalimide luminescent groups were designed and synthesized.The effects of different structures of the two compounds on their fluorescence properties were mainly studied,and it was found that the AIE properties of the compounds could be regulated by structural regulation.4,Four benzocrown ether-based unsaturated hydrocarbons compounds（CBC-1,CBC-2,CBC-3 and CBC-4）were designed and synthesized by Knoevenagel condensation reaction with 4-aldehyde benzo-15-crown-5 as matrix.By comparison,it was found that the modulation of the fluorescence wavelength and intensity of the compounds can be achieved by increasing the degree of the conjugation of the compounds,which provides a feasible way for the regulation of fluorescence properties.There are 60 pictures,8 tables,and 85 references in this thesis.