Synthesis And Ion Recognition Of Binaphthol-based Thioseiuicarhazone Fluorescent Sensor

Molecular recognition plays an important role in environmental, life sciences andother fields. In recent years, it has become one of a challenge task, which to establishbionics system by synthetic sensor to study molecular recognition in vivo. Fluorescentsensor are widely used to detect all kinds of metal ions and anions, because of itssensitive, switch function and situ detection. Binaphthol has been widely used in thefield of molecular recognition and chirality catalysis, which with the larger moleculesconjugated system and potentially chirality structure. In this thesis, a series of newfluorescent sensors were synthesized and investigated for their applications indetection of zinc ion and oxalate. The detail are as follows:1. The concept of molecular recognition and the principles of designing sensor werebriefly introduced. In recent years sensors based on thiosemicarbazone for metal ionsand anions are summarized.2. New binaphthol derivatized thiosemicarbazones L1/L2have been synthesizedand characterized. In DMSO-HEPES (1:1, v/v, HEPES1.0×10-2mol/L, pH=7.4)buffered solution, L1/L2exhibited a selective fluorescent recognition to Zn2+overother tested metal ions with a significant fluorescence enhancement at550nm. IRspectroscopy experiments proved that isomerization phenomenon occurred afterthiosemicarbazone bind Zn2+ions. They could be used for biological applications.3. New binaphthol derivatized based on bis-thiosemicarbazone L3/L4has beensynthesized and characterized. In DMSO-HEPES (1:1, v/v, HEPES1.0×10-2mol/L,pH=7.4) buffered solution, L3/L4exhibited a selective fluorescent recognition toZn2+over other tested metal ions with a significant fluorescence enhancement at572nm and red shift. They would be used for water quality testing and clinicalapplications, which detection limit of them were6.31×10-6M and3.54×10-6M.4. A new sensor LZ1, that was designed with complex of L3and Zn2+, wasrecognized for dicarboxylates. In DMSO-HEPES (1:1, v/v, HEPES1.0×10-2mol/L,pH=7.4) buffered solution, LZ1exhibited a selective fluorescent recognition tooxalate over other tested anion with a significant fluorescence quenched. LZ1has a high sensitivity to oxalate with a detection limit of6.31×10-6M and binding constantof1.8×105M-1.