Synthesis Of Chiral Tetraphenylethene Diamine With Aggregation Induced Emission And Investigation On Chiral Recognition

Fluorescence sensor with aggregation induced emission characteristic for its efficient,responsive, accurate, has demonstrated its unique advantages of chiral recognition.Fluorescence sensor with aggregation induced emission characteristic for its efficient,responsive, accurate, has demonstrated its unique advantages of chiral recognition. Ourgroup combined the characteristics of chiral molecules and AIE molecules for thedetermination of enantiomers of chiral recognition and purity. A new variety of AIEmolecules was first designed and synthesized, and investigated on its selectivity,applicability and Chiral recognition mechanism of action.（1） The chiral tetraphenylethene annular chrial amine derivatives （1S,2S）-7and （1R,2R）-8which contained an optically active cyclic diphenylethanediamine was first designedand synthesized, their structures were characterized by¹H-NMR,¹³C-NMR, IR, MS, andtheir typical aggregation-induced emission characteristics were investigated byfluorescence spectrum.（2）（1S,2S）-7could be occured selective aggregation with chiral acid or amino acidenantiomer by adjusting the relative ratio of the mixed solvent of THF and water, the roleof the two enantiomers occured a significant fluorescence intensity differences. This articlefirstly investigated chiral amino acids as chiral recognition of guest molecules, andfluorescence difference between the partial amino acid enantiomers was up to5.7timeswith the wide applicability, selective and reproducible performance. NMR titrationrevealed the complex proportion between the mandelic acid molecule and （1S,2S）-7is1:1,FE-SEM and TEM revealed the morphology of the aggregates which formed with R/S-mandelic acid;2D NOESY NMR spectroscopy reasonably explained the mode of actionbetween the （1S,2S）-7and R/S-mandelic acids.（3） Three Chiral amino alcohol derivatives D-9、L-9、（1R,2S）-10based on tetraphenylethene with Aggregation-induced emission characteristics have beensynthesized, their structures were characterized by¹H-NMR,¹³C-NMR and IR.¹H-NMRtest found that D-9which contain only one phenyl group showed more widelyrange ofadvantages by using NMR identification of chiral molecules than （1S,2S）-7and （1R,2S）-10.