| Perylene imide and their derivatives exhibited broad application prospects in the field of luminescence due to its large plane conjugate structure,good photothermal stability and high fluorescence quantum yield.Rare earth elements and their complexes showed unique energy level structure,high luminous efficiency and high light conversion efficiency.In this thesis,perylene diimides?PDIs?was modified at the bay position by N-Heterocycle via C-N coupling reaction,and the effects of N-Heterocycle on the optical properties of PDIs were investigated.Eu????TTA?3?N-phen-PDI-?HHP?2?was synthesized,and the fluorescence resonance energy transfer effect of the complex was evaluated through the tests of optical properties.1.1,7-Dibromo-N,N?-dibutyl-3,4,9,10-perylene imide?PDI-Br2?was synthesized from perylene-3,4,9,10-tetracarboxylic dianhydride?PTCDA?.1,7-Di?tetrahydropyrrole?-N,N?-dibutyl-3,4,9,10-perylene imide?PDI-?THP?2?,1,7-di?hexahydropyridine?-N,N?-dibutyl-3,4,9,10-perylene imide?PDI-?HHP?2?and 1,7-di?hexamethyleneimine?-N,N?-dibutyl-3,4,9,10-perylene imide?PDI-?HMI?2?were synthesized by means of 1,7-substitutionwith N-Heterocycle?tetrahydropyrrole,hexahydropyridineand hexamethyleneimine?via C-N coupling reaction,respectively.The structures of PDI-Br2,PDI-?THP?2,PDI-?HHP?2 and PDI-?HMI?2 were characterized through 1H NMR,13C NMR and MS spectra.The optical properties of PDIs were investigated utilizing ultraviolet-visible spectrophotometry?UV-Vis?and fluorescence spectrophotometry?FL?,and the values of fluorescence quantum yield were determined using Reference method.The results showed that the maximum absorption wavelength(?max)of PDI-?THP?2,PDI-?HHP?2 and PDI-?HMI?2 in dichloromethane are 699,683 and 708 nm,and the maximum emission wavelength(?em)are 735,753 and 752 nm?with excitation wavelength at 430 nm?,respectively.The?maxax and?emm of PDI-?THP?2,PDI-?HHP?2 and PDI-?HMI?2 in dichloromethane were obvious bathochromic shift compared with those of PDI-Br2 in dichloromethane(?max=523 nm,?em=549 nm).The effect of the dipole moment of solvent on?max,?em and?35?l?Stokes shift?of PDI-?THP?2,PDI-?HHP?2 and PDI-?HMI?2 was obvious,and the values of fluorescence quantum yield of PDI-?THP?2,PDI-?HHP?2 and PDI-?HMI?2 in different solvents were significant lower than those of PDI-Br2.2.Eu????TTA?3?N-phen-PDI-?HHP?2?was synthesized from 1,10-phenanthroline?Phen?,2-thenoyltrifluoroacetone?TTA?,PDI-?HHP?2 and EuCl3·6H2O,and characterized through FTIR,1H NMR and MS spectra.The optical properties of the complex were evaluated utilizing UV-Vis and FL.The results showed that Eu????TTA?3·2H2O exhibited strong light absorption at 340 nm and strong fluorescence emission at 612 nm,N-phen-PDI-?HHP?2 showed strong light absorption ranging from 550 to 850 nm and strong fluorescence emission ranging from 690 to 850nm,and Eu????TTA?3?N-phen-PDI-?HHP?2?obtained a wide absorption band in the ultraviolet-visible and near-infrared region.According to the investigation of the fluorescence spectra(?ex=340 nm)of the mixture of PDI-?HHP?2 and Eu????TTA?3?phen?,N-phen-PDI-?HHP?2 and Eu????TTA?3?N-phen-PDI-?HHP?2?,it was present that Eu????TTA?3?N-phen-PDI-?HHP?2?exhibited fluorescence resonance energy transfer effect. |
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