Design, Synthesis And Properties Of Functional Organic Molecules Containing 1,4-disubstituted-triazoles Or Tetraphenylethylene

The 1,4-disubsititued-1,2,3-triazoles generated by Cu(I)catalyzed cycloaddition of organic terminal alkynes and azides(the CuAAC)reaction has been widely used in many areas,such as molecular biology,supramolecular assembly,novel medicine design,opto-electronical materials,for its unque stability and aromatic peoperties,and the five mebered ring can act not oly as a linker group but also as a ligand part.The Agrregation Induced Emission materials(AIE material)has been attracted much more attention due to their ultra high luminescent efficiency in the aggregation state,especially in the solid state.And the tetraphenylethene contained organic molcules has become an outstanding representative of AIE materials,due to the twisted molecular conformation of tetraphenylethene,hampers the intermolecular ?-?stacking interaction of organic luminogens.For these structure features of1,4-sisubsituted-1,2,3-triazole and tetraphenylethene,23 compounds has been designed and synthesized in this thesis,and their photophysical properties as well as the relationship between their molecular structure and properties has been carefully examined and investgated.The main contents of this paper has been described as following four parts:In the first part(Chap 2),four organic luminogens containing carbazole group as functional fluorescent chromophore has been obtained via CuAAC reaction,the 1,4-disubsituted-1,2,3-triazole moieties in these molecules acts as a linkage.The results indicated that the “Z” shaped compound II-3 exhibit the most excellent photophysical properties,which means the steric effect should also be considered as well as the electron effect,when optimizing materials containing such structures.In the second part(Chap 3),five fluorescent probes has been designed and synthesized via CuAAC reaction,the 1,4-disubsituted-1,2,3-triazole unit in these compounds act as a linkage,and also a ligand part to participate the ion recoganization,the selectivity of these 5 compounds to different metal ions has also been examined.The spectrum results showed that the III-1 is a well fluorescent probe for Fe3+.In the third part(Chap 4),two tetraphenylethene derivatives containing naphthalene group has been rational designed and synthesized,based on our previous work.They all showed AIE effect due to the introduction of TPE in structure,and IV-2 could also exhibit the luminescence of naphthalene in the single molecular state,it also showed selectivity to Fe3+.In the final part(Chap 5),a series of ?-shaped “push-pull” benzofluorenone derivatives has been designed and syntheised by Suzuki coupling.The photophysical properties of these twelve compounds has been carefully examined.The bromo atom dramatically enhanced their fluorescence,these may cased by the intramolecular n-?interaction.The Solvatochromism of compound V-1-V-4 has also been explored.