Synthesis And Properties Of Small Molecule Fluorescent Probes

Flurescent probe which has the Specific recognition of metal ions or anions or molecules is composed of recognition groups and fluorescent signal response groups. Among them, recognition groups decide the selectivity of different object and fluorescent signal response groups can change the recognition information into fluorescent signal. The small molecule fluorescent probe is ease to be synthesized, low cost, simple structure and superior performance et. 1,8-naphthalene usually has a strong yellow-green fluorescence, high fluorescence quantum efficiency and large Stokes shift, apart from these, it also has good light stability and thermal stability. In recent years, a large number of reports about the modifications and complexes of 1,8-naphthalene were reported. The coordination structure of 1,8-naphthalene can be modified by introducing substituent or functional group in order to get more flexible fluorescent probe. The modification of 1,8-naphthalene was mainly in the 4th position in its positions where can be functionalized.Coumarin derivatives have strong fluorescence, good light stability, adjustable photophysical and photochemical properties, high fluorescence quantum efficiency and large Stokes shift. It was often used as fluorophore in a fluorescent molecular probe. The Fluorescence strength of coumarin can change largely by introducing electron withdrawing group or electron donating group in order to get more fluorescent probe reagent. Now the reports about coumarin derivatives are mainly in 7-diethylamino coumarin aldehyde and 3-amino-3-methyl-7-hydroxy-coumarin aldehyde.In this paper, the research development of naphthalimide and coumarin were outlined. The structure advantages and action principle of the target probe were also described. As naphthalimide and 7-hydroxy-8-aldehyde- coumarin type fluorescent probe?s superior performance and the limited reports, So in this article: A flurescent probe which use 1,8naphthalimide as fluorophore and three-aminoethyl amine as molecular framework was designed and synthesized; A flurescent probe which use 7-hydroxy-8-aldehyde coumarin as fluorophore and ethylenediamine, carbohydrazide, hydrazide, thiosemicarbazide and three-aminoethyl amine as molecular frameworks was designed and synthesized. These flurescent probes have high sensitivity and selectivity response to metal ions and anions. Around this purpose, this thesis researched the following areas:Part 1:a tripod type naphthalimide fluorescent probe which use 4-bromo-1,8-naphthalic anhydride as raw material and designed and synthesized by substitution reactions and condensation reactions. The structure of it was characterized by IR, NMR and ESI-MS et.Part 2: four symmetric, one asymmetric, two tripod type coumarin fluorescent probes which use 7-hydroxy- coumarin as raw material and reacted it with symmetrical ethylene diamine, carbohydrazide, hydrazine, thiosemicarbazide and tripod type of triethanolamine, ammonia and so on. The structure of it was characterized by IR, NMR, ESI-MS et.Part 3: the identify properties of anionic and cation were studied by UV- visible absorption spectroscopy, fluorescence spectroscopy. Naphthalimide probe(1) can better discern Al3+, Cr3+. Symmetric coumarin schiff probe(4a) has a good recognition of Mg2+, F- in DMF as solvent; and as a good recognition of Zn2+ in DMF/H2O=1/4 as solvent. The stoichiometry, constant and mechanism of action of probe and ions were determined by spectral titration, IR, 1H NMR, ESI-ES and ITC et.