Several Construction And Characterization Of Fluorescent Probes Based On Perylene Derivatives

Inspired by intriguing application in molecular electronics, light energy conversion, photocatalysis, and artificial photosynthesis, the photoinduced energy and electron transfer in donor-acceptor systems attract extensive attention. As an important class of functional materials, perylene bisimide derivative possess many advantages of stable structure, oustanding photoelectron properties, high thermal stability and exhibit wide absorption and emission bands in the visible region, which can be widely used in organic solar cell, organic solid state photovoltaic device, organic thin-film field-effect transistor and so on. In this paper, a series of high-soluble and high fluorescent perylene derivatives have been designed and synthesized. Then the characters used for fluorescent probe were researched.Chapter 1: The research and applications of fluorescent probe and perylene derivatives have been reviewed in Chapter 1. The fluorescent probe based on the preylene derivatives is the novel innovation.Chapter 2: Several ways to solve the water-solubility and high fluorescent quantum yield of perylene derivatives were designed and at last an ideal compound 3,4:9,10-perylene tetracarboxylic ammonium was acquired which owned all the excellent characters used as the fluorochromes for staining of living cells. The reasons why it had both the water-solubility and high fluorescent quantum yield were analyzed and a rational reason was acquired. The four hydrophilic carboxyls increased the water-solubility and also increased the strong negative electrostatic potential of the perylene core to prevent the aggregation. The experimentation staining on hippocampal neurons indicated the perylene derivative could be used as good fluorescent label.Chapter 3:Novel fluorescent pH sensor with tunable response range was designed based on high fluorescent 3,4:9,10-perylene tetracarboxylic ammonium, which could coordinate the paramagnetic Fe³⁺ ions to switch off itself by PET quenching and could release Fe³⁺ to turn on the fluorescence again by forming Fe(OH)3 at higher pH and at even higher pH in the presence of different ligands in aqueous solution.Chapter 4:Novel fluorescent switch was constructed based on 3,4:9,10-perylene tetracarboxylic ammonium in presence of diamagnetic Fe²⁺ or paramagnetic Fe³⁺. The switch turns off in presence of paramagnetic Fe³⁺ owing to the PET quench. While it turn on in presence of diamagnetic Fe²⁺ because of the presence of the PET quench. The magnetism transfer between Fe²⁺ and Fe³⁺ can be used to detect H₂O₂ and Vc.Chapter 5: Three types of perylene imide derivatives containing pyridine substituents were synthesized. The high fluorescent perylene imide derivatives can be quenched by coordinating several metal ions. The solvent effect was studied. Among that, 1,7-2(3-hydroxy-pyridine)-N,N'-2-cyclohexyl-3,4:9,10-perylene imide demonstrated sensitivity to the Cu²⁺ and oxidative or acidic gas. The mechanism was researched and a novel probe for the harmful oxidative or acidic gas was designed.