Synthesis Of Pillarene Derivatives And Preparation Of Their Hybrid Materials

Macrocyclic compounds, i.e., crown ether, cyclodextrin and calixarene, play akey role in organic supramolecule chemistry. In recent years, pillarenes as a newclass of synthetic macrocyclic hosts have received considerable attention because oftheir special chemical structures and excellent host-guest properties. Pillarenes canbe easily modified owing to the hydroxyl groups distributed on both rims, hence,many pillarene derivatives have been synthesized and investigated. Colloidalsemiconductor quantum dots (QDs) still represent one of the attractive developingresearch fields of nanotechnology, owing to their advantageous optical propertiessuperior to conventional fluorescent dyes. Magnetic Fe3O4nanoparticles have beengradually applied to catalysis and magnetic solid-phase extraction due to their easyliquid-solid separation. In this thesis, a series of pillarene derivatives weresynthesized, and hybrid materials of pillarene derivatives and the above inorganicnanoparticles were prepared and shown applications in sensors, assembly andabsorbent. Moreover, pillarenes and tetraphenylethene were conjugated throughcovalent bonds to result in tetraphenylethene-bridged pillarenes withaggregation-induced emission (AIE) properties. The following three main researchworks were included.In the first part, by optimizing the reaction conditions, simplifying the reactionsteps, a series of pillarene derivatives were designed and successfully synthesized,and characterized with1H NMR,13C NMR, and MALDI-TOF for the furtherexperiments.In the second part, hybrid materials of pillarene derivatives and quantum dotsor magnetic Fe3O4nanoparticles were prepared. CP[5]A was modified on the surfaceof quantum dots via a ligand-exchange method to improve the physicalopticalproperties, and this composite showed potentials in herbicide detection. Meanwhile, CP[5]As were modified on magnetic Fe3O4nanoparticles via covalent bond asabsorbents for magnetic solid-phase extraction of herbicides.In the third part, a novel bridged pillarene derivative ((P[5]A)4-TPE) wassuccessfully synthesized via covalent bond, which showed remarkable AIE propertyin the mixture of THF and H2O. Meanwhile, The supramolecular assembly of(P[5]A)4-TPE and guest, via host-guest inclusion complexation, leads to aremarkable fluorescence emission enhancement in CHCl3. In addition, thishost-guest system showed reversible temperature responsiveness in solution,offering them great potential as temperature sensor.