The Synthesis Of [2] Rotaxane System Base On Crown Ether

Mechanically interlocked molecule is an important species of artificial molecular machine, in which a number of discrete molecular units assemble together through the weak interaction to achieve particular functions. There are generally three types of molecular machines:rotaxane, pseudorotaxane and catenane. Molecular machines can be driven by external chemical, electrochemical and photochemical stimuli and their output signals are mainly characterized by means of NMR spectroscopy, UV-vis absorption spectroscopy, fluorescence spectroscopy, cyclic voltammetry, circular dichroism and so on. Because of their outstanding properties, molecular machines have a lot of applications in information processing, high-density storage materials and molecular motors, etc.This dissertation investigated the synthesis and assembly of [2]rotaxane molecular shuttles base on the interaction between dibenzo-24-crown-8(DB24C8) and dibenzylammonium (DBA) station.In Chapter2, we synthesized a [2]rotaxane molecular shuttle containing a di-ferrocene-functionalized DB24C8macrocycle, which is interlocked onto a dumbbell-shaped thread component terminated at one end by anthracene fluorophore and at the other end by3,5-dimethoxybenzene. In this rotaxane, we expected that the movement of macrocycle can influence the fluorescence of anthracene fluorophore by the distance-dependent photoinduced electron transfer (PET) process between ferrocene and anthracene. However, the rotaxane system did not achieve this goal.In Chapter3, we synthesized a [2]rotaxane molecular shuttle, in which naphthalimide-functionalized DB24C8is used as the macrocycle and disulfide bond was introduced into the dumbbell-shaped compound to achieve the assembly on gold nanoparticles (AuNPs). The assembly of target rotaxane on AuNPs was also explored. The follow-up work is still in progress.Chapter4is other work.