Synthesis Of Perylene Derivative Double Substituted At The Same Side As Flu Orescent Probes By Cooperative Recognition To Ions

Perylene derivatives,due to their unique structural characteristics,have very good photophysical and electrochemical properties,and are widely used in other scientific and technological fields such as fluorescent probe materials and solar cells.Compared with other perylene derivatives,perylene diimide derivatives are easier to synthesize and have stronger derivatization ability.However,because its molecules are almost on the same plane,the solubility is poor,and the common methods to increase its solubility are:(1)derivatization at the imide position(2)derivatization at the bay position.Perylene tetracarboxylic acid ester derivatives have four ester groups at the end positions,which increase the solubility of the perylene molecular matrix,and expand the application range of perylene derivatives.On the basis of our previous research work on perylene derivatives and the existing work of this research group,this thesis studies a series of bay-substituted perylene tetracarboxylic acid ester derivatives and bay-substituted perylene diacyl A series of imine derivatives.Based on the newer perylene derivatives synthesized in this article,we have designed and synthesized several fluorescent probes with high sensitivity and selectivity for copper ion,fluoride ion and zinc ion.And their chemical properties were studied.The thesis mainly includes the following contents:1.The synthesis and characterization of perylene derivatives containing bipyridine-like units on the same side bay position and the collaborative recognition of different ionsUsing perylene tetracarboxylic acid ester and perylene diimide as a starting point,probe molecules with pyridine-like units and hydroxyl(-OH)double recognition groups on the same side of the bay position were synthesized through nitration reaction and intramolecular rearrangement reaction.;For comparison,perylene tetracarboxylic acid ester derivatives and perylene diimide derivatives with single pyridine-like unit and hydroxyl(-OH)were synthesized.These derivatives have been structurally characterized by hydrogen nuclear magnetic spectroscopy,carbon nuclear magnetic spectroscopy,and mass spectrometry.Studies have shown that perylene tetracarboxylic acid esters and perylene diimides connected to the same side of the bay position with pyridine-like units and hydroxyl(-OH)groups have a synergistic recognition effect on copper ions,fluoride ions,etc.,better than a single connection Contrasting molecules of the same kind that recognize groups.In comparison,perylene tetracarboxylic acid ester has a better recognition effect on copper ions and perylene diimide on fluoride ions.2.Synthesis,characterization and synergistic recognition of perylene tetracarboxylic acid ester derivatives containing dimethylpyridine amine group at the same side bay positionDesigned and synthesized several perylene tetracarboxylic acid lipid derivatives containing lutidine amine groups at the bay position,and studied their response to metal ions.It was found that these probes were fluorescent after acting on zinc ions.Changes are highly sensitive and selective.Using theoretical calculations,several probe molecules were studied and compared to further reveal the structural characteristics of the probes.