The Synthesis And Properties Of Amino-Substituted Benzophosphole

Benzophosphole is an important luminescent moiety,which has been applied in OLED,biological detection,solar cells and other fields.Its photophysical properties can be adjusted by derivation and 2,3-position substituted benzophosphole has been extensively studied due to their easy synthesis,but derivatization of other positions is rarely involved.In this thesis,three structurally diverse NH2-benzophospholes were obtained from cycloaddition of readily available o-aminophenyl phosphine oxide with alkynes.The three series of compounds could be simply separated by column chromatography and showed different photoelectrical properties,which laid a foundation for the correlation study of structural and properties.In the first chapter section 1,the synthesis of benzophosphole is summarized.In the second section,the properties and applications of benzophosphole derivatives are briefly introduced.In chapter 2,three amino substituted benzophospholes are obtained by reaction of(ortho-Boc-aminophenyl)(phenyl)phosphine oxide with alkynes in the presence of AgOAc.The UV-Vis and fluorescence spectra of these compounds were characterized and analysed,and the results indicated that these compounds have regular photophysical properties.Among them,4-substituted products showed strong fluorescence emission and higher fluorescence quantum efficiency,and have the obvious solvation color effect,the addition of amine groups extended π conjugate system,and formed an effective intramolecular charge transfer(ICT)effect with P=O group,resulting in obvious red shift of their UV-Vis absorption and fluorescence emission.These properties make them potentially useful in organic functional materials.