Synthesis And Properties Of Several Novel Perylene Derivatives With Recognition

Perylene derivatives are polycyclic aromatic hydrocarbons with extended π-conjugation and intense absorption and emission properties. Perylene diimide (PDI) derivatives have been studied more extensively because of their rigid planar backbones and outstanding optical and electronic properties. In addition, PDIshave been widely employed as promising active elements in organic solid materials areas, such as photovoltaic devices, organic field effect transistors (OFETs),and electrophotographic devices. In order to improve the properties of PDIs, developing new derivative methods of perylene becomes increasingly important.Based on the current investigation of perylene derivatives, this thesis developsseveral new synthesis methods and designs a series of molecular fluorescent probes. The main contents are as follows:The first chapter：the developments and design principle of fluorescent molecular probes and the synthesis methods and applications of perylene derivatives were briefly reviewed. Research topic of this thesis was proposed.The second chapter: a new reduction reaction of nitro-perylene derivativeshas been developed to synthesize amino and hydroxyl substituted perylene derivatives with high yield. The first example of oxazepin ring formation involvinga Schiff base were observed at the sterically crowded bay area of electron-deficient perylene diimide. The photophysical properties and detection of metal ions of as-prepared compouds were also investigated.The third chapter: a new cyclization reaction based on perylene diimide (PDI) derivatives has been developed. A series of pyridine moieties containing perylene diimide (PDI) derivatives were synthesized and the optical properties were researched in detail.The forth chapter: a new nitroxide radical incorporating with amino grouphas been synthesized using Gabriel synthesis. In addition, a molecular fluorescent probe incorporated with pyridine and nitroxide radical based on PDI was s ynthesized to detect paramagnetic metal ions.