Synthesis And Properties Of Diarylethene Fluorescent Molecule Switches Based On Perylene Monoimide

As their unique photochromic properties based on light regulating, photochromic compounds had rapidly caused extensive concern of scientific researcher since they were discovered. With the wide application of fluorescent probes in various fields, fluorescent molecules capable of optical switch materials have become the focus in the current. In the numerous organic photochromic compounds, diarylethanes were favored by many scholars on account of their good thermal stability and fatigue resistance. This thesis focuses on the properties of biological incompatible, low fluorescent quantity and low fluorescent switch ratio of diaylethanes fluorescent molecular switches in the area like biological imaging applied the following innovative experiments:(1) Designed and synthesized three kind perylene monoimide derivatives which have different groups with various electronic effects, to research the effect of different electronic groups and solvent polarity on the fluorescent property of perylene monoimide. The results show that: the compunds with electronic drawing substituents and in the solvent with low polarity have the highest fluorescence intensity, and the compound PMI-Ph-COOH shows the highest fluorescent intensity and fluorescent quantum yield in different solvents.(2) Designed and synthesized perylene monoimide-diarylethane fluorescent switchs monomer, analysis the synthetic method and their optical properties. The results show that: both the three kind compounds have high fluorescent intensity and faster response time, most molecular become closed form after 2 s under 302 nm UV-irradiation, have a high fluorescent quenching efficiency that higher than 60%, after 15 s can be photostationary state and the fluorescent quenching efficiency can be 95%. In the three compounds, PMI-1-DTE has better fluorescent molecular switch properties.(3) Designed and synthesized perylene monoimide-diarylethane fluorescent switchs biocompatible polymer, and research the optical properties of three kind polymers in water solution. The results show that, the three kinds polymer have good optical properties and fatigue resistance, and very short response time, there is a high fluorescent quenching efficiency that can be 60% after 4 s under 302 nm UV-irradiation, after 45 s it can be higher than 95% and be photostationary state. Polymer P1 has the best fluorescent molecular switch properties, and has more potential to be applied to bioluminescene imaging probe.