Preparation And Properties Investigation Of Fluorescent Phosphorimine Derivatives

In this paper,a series of phosphinimine-derivatived compounds with fluorescent properties were successfully synthesized by Staudinger reaction and Kirsanov reaction.The chemical structures,optical properties and ion recognition properties of these compounds were studied here from the following aspects:1 The phosphinimine derivative 2,6-bis(4-triphenylphosphinoiminylidene)-cyclohexanone(M1)was synthesized by the catalyst-free Staudinger reaction.The mixture of M1 and polyfluorene was mixed into water to prepare corresponding nanoparticles(PFO-M1).The optical ionic recognition properties of PFO-M1 were studied by UV and fluorescence spectrophotometers.It was found that the nanoparticle displayed specific response to the addition of Cl O-(the lower limit of detection reached~6.63×10-7 M).The yellow fluorescence of PFO-M1 disappeared and blue fluorescence appeared after adding Cl O-.The ratiometric change has been clearly observed.The addition of other anions,cations and reactive oxygen species(ROS)did not cause sucha significant changes.The possible recognition mechanism was studied by UV and fluorescence spectroscopy.2 A type of phosphinimine-derivatived polymer containing P=N bond,poly-2,6-bis(4-ethylbis(diphenylphosphinoiminobenzylidene))-cyclohexanone(P2),was synthesized by Staudinger reaction.Optical properties and ionic recognition properties of P2 were studied by UV and fluorescence spectrophotometers.It was found that after the addition of Cl O-to P2 solution,the yellow fluorescence of P2 solution quenched significantly(the lower limit of detection reached~2.63×10-8 M).Its fluorescence did not change significantly after adding other anions,cations and ROS.3 A type of phosphinimine derivative containing P=N structure,N-1-naphthyltriphenylphosphine imide(S1),was synthesized by Kirsanov reaction at room temperature.Aggregation-induced emission enhancement(AIEE)characteristic of S1 was observed in DMF-H2 O system with different solvent composition ratio.The fluorescence of S1 was significantly quenched by H+(with the lower limit of detection of~2.5×10-8 M),while the addition of other common anions and cations just brought slight changes in fluorescence.After adding OH-,fluorescence intensity of S1/H+ mixture can be restored,indicating that S1 has the potential to act as reversible p H fluorescence indicator.4 The phosphinimide derivative,2-hexyl-5-(triphenylphosphoranylidene)-1Hbenzo[de]isoquinoline-1,3(2H)-dione(S2),was synthesized by Kirsanov reaction.The optical properties and ionic recognition of S2 were studied by UV and fluorescence spectroscopy.The green fluorescence of S2 was significantly quenched(the lower limit of detection reached~6.98×10-8 M)after the addition of PA.In the presence of other cations and cations,the fluorescence of S2 did not change significantly.When other nitro compounds were added,the dection of PA showed good anti-interference.