Synthesis And Performance Study Of Chiral Fluorescent Molecular Probes

Fluorescent molecular probe has been an important method in the field of molecular recognition due to its high sensitivity, accuracy, high efficiency and real-time monitoring properties. And the recognizedspices include cationic and anionic ions, chiral molecules and so on. People devote themselves on more efficient and practical probe to expand its function to biology, chemistry, medicine and environment, In this study, I design and synthesize two chiral moleculeswith chiral di-naphthalene as the core and molecular functional groups as the binding sites to interact with metal ionsand chiral molecular.The first chapter mainly introduces the mechanism of the fluorescent probe molecule, the research progress of metal ions and chiral molecules, and the advantage of porphyrin structure. The theoretical basis and background for the research provide a good guidance and inspiration for my work.The second chapter synthesize a chiral dinaphthalene fluorescent molecule for cationic probe. Among 11 kinds of metal ions, only Zn2 + and Cu2 + turn the host molecular solution from yellow to pale lemon and reddish, respectively.Also, only Zn2+ can lead to a 6.5 times pronounced fluorescence enhancement. Furthermore, the enhanced fluorescence of Zn2+ can’t be interfered by other metal ions except Cu2+. Meanwhile, the addition of Cu2 + can lead to 30 nm blue shift of the fluorescence spectrum of host and thischange can’t be interfered by Zn2+. Through the change of color and the spectra, the di-naphthalene- pyridine molecules realize the visualization, high efficient and selective recognition of metal zinc ion and copper ion.The third chapter design and synthesize bisporphyrin- dinaphthalene chiral molecules,In which two porphyrin units are attached to a chiral di-naphthalene core. Combined with the advantage of the long wavelength emission of porphyrin and the chiral characteristics of cdi-naphthalene, it can be used as probe of different chiral acid, chiral alcohol and chiral monosaccharide.Through analyzing the change of the absorption spectra, I find that the host moleculescan form 2:1 chiral complexes with Boc-phenylalanine or glucose.The enantioselectivity factorof the host molecules to Boc-phenylalanine and glucose(KD/KL)are 2.59 and 1.73,respectively,showing chiral recognition ability of the chiral host molecules to chiral Boc-phenylalanine and glucose.