| Chemical sensor has excellent performance in metal and chiral organicrecognition due to high selectivity, sensitivity and fast response. It had been widelyused in environmental science, life science and pharmacy. In this dissertation, wesynthesized a porphyrin-BINOL based fluorescent sensor which combinesaxe-chirality of BINOL and π-plane, long-wavelength fluorescence, highfluorescence quantum efficiency of porphyrin. This sensor realizes the recognition ofcopper ion and chiral tartaric acid.In the first chapter, we organized papers of organic fluorescent sensor andproposed the design of porphyrin-BINOL based sensor.In the second chapter, we synthesized chiral small moleculars BINOL-pyridine(BINOL-Py) and Porphyrin-BINOL-pyridine (ZP-Py) through Suzuki coupling andShiff base synthesis. With fluorescence analysis, we noticed that fluorescence ofBINOL-Py could increase by146.73times and the fluorescence quench constanttowards ZP-Py is up to1.39×105through coordination between pyridine, phenolicoxhydryl, carbon nitrogen double bond and copper ion. We also demonstrated thatBINOL-Py and ZP-Py could selectively recognize D-and L-tartaric acid with theirdifferent ability to enter the chiral cavity. The coefficient of enantiomer selection (ef)is up to1.83and2.85, respectively.In the third chapter, we synthesized other five porphyrin-BINOL based sensors byincorporating acetylene bond into porphyrin and BINOL, reducing Schiff base orincorporating thiophene to pyridine. The reduction increases the number ofconfigurations, reduces the rigidity of recognition groups and coordinating abilitybetween copper ion/tartaric acid and ZP-Py, incorporation of thiophene increases thesteric hindrance, both these reduce recognition of guest. We conclude that ZP-Py isthe most efficient sensor of copper ion and tartaric acid in this serie. |
