Synthesis And Characterization Of Novel Triphenyl Imidazole-linked Tailed Porphyrin

Porphyrins and imidazole derivatives have been widely used in the preparation ofphotoelectric materials. According to the reported literatures, porphyrins have lowfluorescene quantum yield and strong self-aggregation in application, however,imidazole derivatives have higher fluorescene quantum yield. If we connectedimidazole derivatives to the meso porphyrin via chemical bonds, not only thephotoelectric properties will be improved, but also the self-aggregation will beavoided.Under the circumstances, three kinds of aromatic imidazolyl tailed porphyrinswere synthesized, and some of their optical properties was researched. The details ofthis thesis are as follows:1. The structures, properties and synthetic methods of porphyrins were brieflyintroduced. Especially, the application and synthetic methods of the tailed porphyrinswere emphasised on.2. Firstly, we synthesized two precursors of the tailed porphyrins:5-p[(4-bromo)butyloxo]phenyl-10,15,20-tripheny porphyrin (BrBPTPP) and5,10,15,20-tetra[(4-bromo)butyloxo]phenyl-5,10,15,20-tetrapheny porphyrin (TBrBPTPP)via the Alder-Longo and Willamson ether synthetic methods. Secondly, wesynthesized the three kinds of tailed porphyrins:5-p{4-[1-(2,4,5-triphenyl)-imidazole]butyloxo}phenyl-10,15,20-tripheny porphyrin (Tri-Ph-ImBPTPP),5-p{4-(2,5-diphenylimidazole)phenoxy]butyloxo}phenyl-10,15,20-tripheny porphyrin (HO-Tri-Ph-ImBPTPP) and5,10,15,20-{4-[1-(2,4,5-triphenyl)imidazole]butyloxo}phenyl-5,10,15,20-tetrapheny porphyrin (Tetra-Tri-Ph-ImBPTPP) via the reaction of the twoprecursors and imidazole derivatives. Thirdly, the fouth tailed porphyrins:5,10,15,20-p{4-(2,5-diphenylimidazole)phenoxy]butyloxo}phenyl-5,10,15,20-tetra-pheny porphyrin (Tetra-HO-Tri-Ph-ImBPTPP) was also probed.3. The structures of the three kinds of tailed porphyrins were characterized byinfrared spectra, nuclear magnetic resonance spectra, and mass spectra.4. The UV-Vis and fluorescence spectra of the three kinds of tailed porphyrinswere also investigated in detail. Taken the TPP as reference in the UV-Vis spectra, itshowed that the Q bands of Tri-Ph-ImBPTPP and HO-Tri-Ph-ImBPTPP took red-shiftobiviously up to5nm, while the Q bands of Tetra-HO-Tri-Ph-ImBPTPP took blue-shift obviously up to4nm. Taken the TPP as reference in the fluorescencespectra, it showed that the Q bands of Tri-Ph-ImBPTPP and HO-Tri-Ph-ImBPTPPtook red-shift at1-2nm, while the Q bands of Tetra-HO-Tri-Ph-ImBPTPP tookblue-shift at2nm. In all, the fluorescence quantum yields of the three kinds of tailedporphyrins were somewhat increased, and the fluorescence quantum yield ofTetra-HO-Tri-Ph-ImBPTPP was the largest.