Synthesis Of Tert-butylspiro-diamines And Study On The Catalytic Properties Of Fluorescent Probes And Small Molecules

Aggregation-induced emission(AIE)is a unique phenomenon that AIEgens show weak fluorescence in solution but strong fluorescence in aggregation.Contray to the traditional fluorescent dyes,AIEgens avoid the ggregation-caused quenching(ACQ)effectively.The Schiff base derivative,which is obtained by simple condensation between salicylaldehyde and amino groups,is a class of molecules with such unique luminescent properties.Induced by the intermolecules hydrogen bond between Schiff base’s nitrogen and ortho-hydroxyl groups,a stable six-membered ring makes the whole molecule free to be blocked,thus leading to the luminescence characteristics of aggregation-induced fluorescence.In this paper,based on the structure of the spirobifluorene,salicylaldehyde is introduced to construct a new type of aggregationinduced luminescence system,which would have a greater prospect in the development of new fluorescent probe and solid luminescent materials.In addition,the small molecular catalytic properties of chiral spiramine compounds were explored.The work of this paper is divided into the following two parts:In the first part,two Schiff base fluorescent probes SPF-T1 and SPF-T2 with aggregation-induced luminescence properties were synthesized.First,the recognition of metal ions was studied by using Schiff base SPF-T1 with spirofluorene as a probe.The result of the experiment shows that the probe has the ability to identify copper ions,cobalt ions and zinc ions.The copper ions and cobalt ions has a great impact on the probe absorbtion spectrum,the color of the solution changes from colorless to yellow,and the detection limits are 0.15μM and 0.12μM separately.SPF-T1 shows aggregationinduced fluorescence enhancement phenomenon when Zinc ions is added,the detection limits is 0.3μM.In addition,SPF-T1 is used as a zinc ion probe for cell imaging Furthermore,introduction of the triarylamine units into SPF-T1 structure results in a SPF-T2 with yellow fluorescence in solid state,which is also used as fluorescent enhanced zinc ions probe with the detection limit of 0.15μM.The cobalt ion and copper ion were detected bu UV detection at a limit of 0.084μM and 0.073μM respectively.Its aggregation induction performance is more obvious and has two-photon absorption performance.In the secend part,chiral spiramine compounds are applied to small molecules asymmetric catalytic reation,for the development of new catalyst.Michael addition and Friedel-Crafts reaction are catalyzed successfully.The yield is 75% and 86% respectively,but there is no better performance in asymmetric catalysis.