Synthesis And Properties Of Two New Isoindole-based Fluorescent Dyes

Isoindole is one of the most important aromatic heterocyclic compounds in the 10? system,and its derivatives are widely used in nature and dye molecules.Over the past few years,isoindoles have found wide application in materials' science.Isoindole containing BODIPY dyes have long wavelength absorption/fluorescence emissions,high fluorescence quantum yield s and have been extensively used in biological imaging,new standard luminescent dyes and so on.In this thesis,two series of isoindole-based derivated dyes were synthesized.In charpt 1: a one-pot synthesis of a series of N2O-type benzopyrromethene boron complexes has been achieved from the condensation of pyrrole,formylisoindole and various boronic acids.X-ray structures indicate that the boron atoms in these dyes adopt a tetrahedral arrangement and the connected axial substituted groups are in the apical site of the pyramidal arrangement.These dyes enjoy a set of excellent photophysical properties including red/near-infrared absorption,high solution-and solid-state fluorescence,as well as good solubility in variety of solvents due to the presence of axial substituted groups,which provide sterical protection and prevent their possible aggregations.Two water soluble derivatives with pyridinium ions were synthes ized and used as near-infared excitable mitochondrially lacolizing fluorescent probes.In charpt 2: we also synthesized a series of small-molecule fluorescent dyes with Push-Pull effect by Vilsmeier-Haack reaction,Suzuki and Knoevenagel reaction.X-ray structures indicate that the isoindole,N,N-two methyl benzene,propyl two nitrile are almost in the same plane.These dyes are poor solubility due to the high conjugated rigid plane,so we have improved the solubility by introducing alkyl chain on the N atom of isoindole.Their structures were identified by 1HNMR,13 CNMR,mass spectrometry and X-ray diffraction.On this basis,their spectral properties were s tudied.These compounds are expected to be used as solar cells and NIR contrast agents for biomedical applications.