Synthesis Of A Calix[4]Arene Tartaric Acid Derivative And Chiral Recognition

Supramolecular self-assemblies have potential application in drug delivery, nanomaterial preparation, selective catalysis, or cell mimicry and so on. So supramolecular self-assemblies have attracted great attention from chemists and they are one of topic current interests. Calixarenes can include guest molecules and have much dominance in the field of self-assembly because of their hydrophobic cavities and easy chemical modification. The synthesis, self-assembly and molecular recognition based on a new chiral calix[4]arene tartaric acid derivative have been studied in this thesis. The results conclude the following main points:1. A new calix[4]arene tartaric acid derivative 5 with alkyl at the upper rim and L- tartaric acid residual substituted in 1, 3 position at the lower rim was designed,synthesized, and characterized by 1HNMR, 13CNMR and IR spectroscopy.2. (1S, 2S)-1, 2-diphenylethylenediamine,(1R,2S)-2-amino-1,2-diphenylethanol, R-α-methybenzylamine,and S-α-Phenylglycinol could be assembled nanofibers and nanosphere with this calix[4]arene tartaric acid derivative 5. The gelation and turbidity behaviors of the complexes were tested in various organic solvents.3. The chiral recognition behavior of this chiral calix[4]arene derivative 5 for R /S-α-methybenzylamine, R/S-α-phenylglycinol, (1S,2R)/(1R,2S)-2-aminol-1 ,2-diphenylethanol, (1R,2R)/(1S, 2S)-1, 2-diphenylethylenediamine was studied by Fluorescence spectroscopy and 1HNMR spectroscopy. The results suggest that the recognition of those chiral molecules can be realized by the method that testing the change of Fluorescence intensity after adding calix[4]arene 5 to their soluntion. Meanwhile, Association constants of some complexes were calculated by Fluorescence titration.