Host-guest Chemistry And Antibacterial Activities Of Water-soluble Pillararenes

Pillararene is a new type of macrocycle.It has been extensively investigated over the past years in material,biology and pharmacy fields,due to their versatile accessibility and chemical modifiability.This thesis mainly studied the host-guest,anti-bacteria abilities of water-soluble pillar[5]arenes and self-assembly of copillar[5]arenes.The cyclization of several kinds of BINOL ethers were also investigated.（1）We synthesized three water-soluble pillar[5]arenes with different hydrophilic groups.The pyridinium-based pillar[5]arene and trimethylammonium-based pillar[5]arene has shown very different abilities in complexation of total hydrophobic guests in water and in antibacterial effect against Pseudomonas aeruginosa.The pyridinium-based pillar[5]arene exhibited good inhibition activity with the minimum inhibitory concentration（MIC）0.051 mmol/L,while no significant antibacterial and biofilm formation activity for trimethylammonium-based pillar[5]arene was observed.（2）We synthesized two kinds of monofunctional copillar[5]arenes with different length linkers.Single crystal structures of 3.2b,3.4 and 3.5 were obtained by slowly evaporation their solutions,respectively.We concluded that,when there is no conformational limits and competitive guests,the self-assembly manner of a supramolecular AB type monomer in the solid state was mainly dependent on the strength of the interactions between its host part and its guest part.（3）We tried to prepare novel macrocycles based on different axial chiral1-（2-hydroxynaphthalen-1-yl）naphthalen-2-ol（BINOL）ethers.However,we found that,only parts of these ethers can be connected by paraformaldehyde and BF₃·OEt_2,while only linear dimers and trimers were separated successfully.Cyclic tetramers and hexamers could only be observed in the ESI-mass spectra,because of their very low yields.