Self-aggregation And Ion-Recognition Study Of Phenanthridines Dyes

Hydrogen bond is a weak force presence between Hydrogen atom and electronegative atom,and wide spread in naturalworld and synthesized molecules.H-bonding is a research hotspot because of a vial factor for physical,chemical and optical properties of materials.On the basic of Hydrogen bond,a series of phenanthridines derivatives PHE1-PHE6 and reference REF1-REF6 obtained by one-pot method at room temperature and acid-free condition.The properties and of target molecules were researched detailedly in this thesis including the following parts:?1?Structural effect of excited state intermolecular proton transfer?ESPT?in organic chromophoresESPT phenomenon in organic chromophores PHE1-PHE6 containing phenanthridine segment has been surveyed.There are few studies on synthesis of phenanthridine in mild strategy have been performed and we presented a mild strategy to prepare phenylphenanthridin dyes by one-pot reaction in yields of 62%-78%,and a mechanism was proposed.In the end,the target dyes?PHE1^PHE6?and corresponding reference alkylate dyads were prepared?REF1^REF6?.In addition,the relationship between the chemical structures of the target dyes and ESPT reaction was characterized by X-ray single crystal diffraction,NMR spectra,SEM,TEM,UV/visible spectra,the steady fluorescence spectra,Molecular geometry optimization the property of aggregation induced fluorescence enhancement?AIEE?.The results indicated that intermolecular hydrogen bond was affected by the substitutents.The UV/visible spectra of target dyes PHE1^PHE6 showed that PHE1^PHE6 displayed a new absorption peak at 350 nm in DMF,ACN and protic solvents.The steady fluorescence spectra of target dyes PHE1^PHE6 suggested that PHE1^PHE6 could undergo ESPT in DMF,ACN,and produce dual-fluorescent emission.Besides,the ESPT ability of organic chromophores showed high dependency with the concentration.Furthermore,the target dyes PHE1-PHE6 displayed obvious AIEE effect and formed nano-aggregation in benign solvent/nobenign solvent?ACN/H₂O?.?2?Detection of metal ionOn the optical property research of phenanthridine,we discussed the detection effect to metal ion of PHE1-PHE6.The results implied that PHE1 has well recognition ability for Fe³⁺,and the UV/visible spectra,the steady fluorescence spectra,SEM were employed to explore the recognition capability of PHE1 to Fe³⁺,and showed that PHE1has linear recognition for Fe³⁺.The quenching constant K is 3.2×10³ M^-1 revealed that PHE1 could form stable complex with Fe³⁺.Therefore,PHE1 could apply to alternative recognition for Fe³⁺.