Synthesis And Covalent Immobilization Of Naphthalimide And Other Derivatives As New-type Fluorescence Carriers For Optical Fiber Chemical Sensor Preparation

One of the most important aspects of fluorescence chemical sensor research is searching new fluorescence carriers for molecular recognition. The fluorescence carriers for preparing sensors are limited to a narrow range of chemical compounds and most fluorescence carriers are physically entraped in various membrane materials. Although physical entraping is a simple method for sensor membrane preparation,the leaching of fluorescence carrier is a major disadvantage. A central research topic is searching new fluorescence carriers with high sensitivity,good selectivity,excellent reversibility and stability. Along this line,the author of present thesis paid attention to naphthalimide,carbazole and porphyrin derivatives. The naphthalimide and carbazole derivatives as well as covalently immobilized porphyrins have not been reported to data in the literature.In this thesis,new fluorescence carriers with good properties were synthesized and copolymerized under UV irradiation on the silanized glass or quartz disk and -the sensors prepared were studied. (1) N-propyl-4-(N-methylacryloxy-ethyl)amino-1,8-naphthalimide (PMEAN) was synthesized and used for determination of picric acid. The linear range of the sensor is 9.80x10-7-1.96x10-4 mol I-1. The sensor has been used for indirect determination of chloroquine content in pharmaceutical tablets. (2) N-Allyl-4(N-2'-hydroxyethyl)amino-l,8-napthalimide (AHEAN) was synthesized and utilized for nitrofurantoin assay based on fluorescence quenching. Nitrofurantoin can be determined in the range between 1.00x10-6 and 1.00x10-3mol I-1. The sensor has been applied to the analysis of pharmaceutical and urine samples. (3) N-Allyl-4-piperazinyl-l,8-napthalimide (APN) with proton "off-on" switch behavior was synthesized. The sensor can be used for the determination of pH between 10 and 4 and has been applied to the analysis of water samples. (4) N-Allyl-4-(4'-methyl-piperazinyl)-l,8-napthalimide (AMPN) with proton "off-on" switch behavior was also synthesized. The sensor can be used for determination of pH in the range of pH4.5 - 9.0 and has been applied to the analysis of urine samples. (5) N-(2-methacryloxyethyl) benzo[k,l]thioxanthene-3,4-dicarboximide (MBTD) was synthesized. The sensor can be used for determination of 0-25%(v/v) water content in acetone. (6) Meso-tetra(4-allyloxyphenyl) porphyrin was synthesized. The sensor can be used for determination of pH in the range of pH 1.5 - 5.0 and has been applied to the determination of water samples. (7) 9-N-allyl carazole was synthesized and used for direct determination of doxycycline. The determination range is 6.00x10-7 and 2.00x10-3 mol I-1. The sensor was used in the analysis of pharmaceutical preparations and urine samples. In addition,three fluorescence carriers were synthesized,they are allyl ester of rhodamine Rh-Al,3,6-diamino-9-N-allyl carazole,4-methyl-7-allyloxynaphtho[l,2-b]pyran-2-one and have not been prepared for sensors yet.