Studies On The Synthesis And Properties Of Bay-substituted And Cyclized Tetracarboxylic Acid Ester Derivatives

Perylene-3,4,9,10-tetracarboxylic tetraesters, being close relatives of PBIs, are highly valuable organic materials because of their outstanding photoelectric properties since they were discovered. These compounds have better solubility in organic solvents than PBIs which allowed facile purification and further derivation. In addition, they also have large band gap, high extinction coefficient and fluorescence quantum yield, good thermal and optical stability. These properties make them ideal materials for application in the field of organic photovoltaics, artificial photosynthesis and nanoelectronic devices. we designed and synthesized a series of conjugated system expanded perylene derivatives and fluorescent probe for detecting fluoride ion based on their excellent chemical properties, The main contents include the following four aspects:In first chapter, the composition and classification of molecular probes have been introduced.The characteristics and practical applications of various types of molecular probes and the development status of perylene fluorescent probes were reviewed, and the common modifying methods were summarized. At last, the research direction and proposed research topic were discussed.In second chapter, a new synthetic method of five membered S- and six membered oxygen-annulated perylene tetraesters derivatives at bay position has been found, thus a novel conjugated system expanded perylene derivatives were developed. This process has an array of advantages, such as simplified operational procedure and novel structure. Through the investigation and the structure of simulated calculation of these compounds, we found they had better optical properties and high solubility.In third chapter, we designed and synthesized a new series colorimetric and ratiometric fluorescent probes which are suitable for detection of fluoride ion based on perylene tetraesters, these sensors with amide groups are highly selective and sensitive for fluoride anion over other halide ions. In these molecules, perylene tetraesters with amide groups in bay position fluorescence quenched when reacted with fluoride anions, but S-annulated perylene tetraesters with amide groups showed different fluorescence.In fourth chapter, we synthesized a series of hydroxyl-substituted perylene derivatives from nitro-perylene tetraesters and analyzed the optical properties of those compounds. we found that these derivatives can perform the selective recognition of fluorine anions through hydrogen bonding with advantages of obvious fluorescence color changes, strong anti-interference ability and high sensitivity.