Design And Synthesis Of Several Novel Fluorescent Probes Based On Perylene Diimide Dyes

Fluorescent probes have many advantages such as high selectivity, good sensitivity, high response speed and easy manipulation. As a result, they have been used in the fields of chemistry, biology, environmental science and so on. Because of their excellent properties and low cost, a large number of researchers play great interests in designing and exploring fluorescent probe complexes for various applications.Iron element is an indispensable element for living organisms, and it plays an important role in maintaining the normal function of every organ. However, both of its deficiency and overload can induce serious disorder and dysfunction to organs. Thus, it is indispensable to detect and determine the amount of iron in our daily life. This thesis summarized the fluorescent probes for Fe3+and selected perylene diimides derivatives as the fluorescent dyes to design and synthesize novel Fe3+fluorescent probes. Perylene diimides have high fluorescence quantum yield and excellent photochemical stability, and it is easy to modify in the "bay region" (1,6,7,12 positions) and amides position. Perylene diimide fluorescent probes have received increasing attention due to their outstanding photochemical stabilities and high fluorescence quantum yield. However, to the best of my knowledge, water-soluble perylene diimides fluorescent probes are rare.In this thesis, firstly, click chemistry was employed to synthesize several Fe3+ receptors, which were condensed with perylenetetracarboxylic dianhydride to afford five novel perylene diimides fluorescent probes. Their response to various metal ions has been explored.Charpter 1 presents an overview of fluorescent probes including their properties, mechanisms, categories, and applications. Speccial attention has been placed on the perylene diimides for fluorescent probe. In the last but not the least, this chapter gives the content and objective of our research.Charpter 2 describes the synthesis and characterization of the two perylene diimide fluorescent probes based on PET mechanism. These two probes with four triethylene glycol or triethylene glycol monomethyl ether chains exhibited a good solubility in aqueous solution. The results showed that they have a high selectivity to Fe3+ in actonitrile, water and 1:1 actonitrile/water mixture. The binding ratio and constant between the probes and Fe3+ were determined via Job plot method and Benesi-Hildebrand equation.Charpter 3 reports the synthesis and characterization of three perylene diimide fluorescent probes based on FRET mechanism. Their response to various metal ions such as Na+、K+、Mg2+、Ca2+、Ni2+、Zn2+|Cd2+、Hg2+、Fe2+、Fe3+、Pb2+、Mn2+| Cu2+、Ag+ has been explored.