Synthesis And Performance Research Of Novel Fluorescent Compounds

The nuclear parent of coumarin derivative is composed of benzopyone. It’s a compound widely existing in the nature environment. It has obvious optical activity and excellent biological activity. The coumarin derivative is extensively applied in various fields and gains increasing attention of scholars from home and abroad due to its outstanding performance. In this thesis, five novel coumarin fluorescent molecular probes are synthesized with diethylamino in position 7 as strong electron-donating groups along with quinoline-2-carbaldehyde, 7-hydroxy-chromen-2-one, thiophene-2-carbaldehyde, 3,5-Dibromosalicylaldehyde, and benzaldehyde, in the position 3 as receptor unit or electron withdrawing group. And their application in metal ions fluorescence analysis field is studied.Rhodamine 6G derivatives have high extinction coefficient and high yield of fluorescence quantum, thus being an important material for making fluorophore molecular probes. Rhodamine 6G derivatives with no toxic and side effect to cells have excellent cell membrane permeability. Therefore, they have good prospect of application in living bodies and living cells. Rhodamine 6G screw amide ring is characterized by colorless and non-fluorescence solution when the five-membered rings are closed. But Rhodamine 6G screw amide ring can be opened and emit fluorescence when there is recognizable object in the environment.The thesis was comprised of four parts.Part 1: Introduction of the design principle of cationic fluorescent probe and reviews the study of cationic fluorescent probe in recent years.Part 2: Design and synthesis of four kinds of coumarin fluorescent compounds containing Formyl hydrazone group which can detect Cu2+. The new compounds are characterized by IR, EA, MS, 1H NMR, 13 C NMR.Part 3: The interaction between FSBA and metal ions are studied. The result shows that FSBA is selectively recognizable for Cu2+, Fe3+ and Ni2+ in the form of fluorescence quenching. And the quenching of FSBA and the Cu2+ is more remarkable with a more noticeable red shift of ultraviolet absorption peak. While the addition of other metal ions, the fluorescence intensity of FSBA has slight changes.Part 4: The interaction between FKBA and metal ions are studied. The result shows that FKBA is highly selective for Cu2+ in the form of fluorescence quenching. While the addition of other metal ions, the fluorescence intensity of FKBA has slight changes.Part 5: By combining two groups containing benzopyrone structure, more intensive fluorescence can be noticed. Lone pair electrons of oxygen atoms in the compound have good complexation with metal ions, which makes benzopyrone structure of the compound more stable, thus intensifying the fluorescence. Therefore it’s promising to synthesize a new fluorescence probe with high sensitivity, strong specificity and good selectivity.Part 6: Rhodamine 6G synthesized lactam structural compounds by means of hydrazinolysis. And the lactam structural compounds exisit in screw amide ring whose relative intensity of fluorescence is zero. While the addion of metal ions to the compound, the nitrogen-atoms in the lactam structure coordinates with the maral ions, leading to the lactam structure ring opened, which causes the fluorescence increasingly intensified, presenting long wave absorption in amaranth. This property of rhodamine makes it possible to synthsize a novel fluorescent reagent with obvious sensitivity and excellent selectivity.