Synthesis And Application Of Sulfonic Pillararenes

Pillararene has attracted increasing attention since it was firstly reported in 2008.In recent years,the researches about pillararenes are not limited to the field of molecular design and synthesis,molecular structure and host-guest property,the researchers focus on the pillararenes practical applications in biomedicine,nanomaterials,smart materials and so on.Due to the excellent properties of pillararenes that allow pillararenes to interact with a series of ?-electron deficient guests and neutral guests via host-guest interactions,such as easy functionalization at both ends of molecules,highly rigid and symmetrical pillar-shaped architecture and ?-electron-rich cavity.Multi-functional pillararenes which modified with diverse functional groups such as carboxyl and phosphoryl groups play an important role in many fields.Thus,it is still a significant challenge to synthesize new functional pillararenes.Available strategies of constructing fluorescent pillararene-based materials are to modify pillararenes with fluorescent molecules or to form complex via host-guest interaction.Therefore,such fluorescent pillararene-based materials can be applied in various fields such as sensing,cell imaging and visualization therapy.In this paper,we synthesized two kinds of novel functionalized pillararenes and their host-guest properties were investigated in detail.Subsequently,these molecules were used to construct fluorescence systems integrated with fluorescent molecules.This paper is divided in to three parts:In the first section,we firstly synthesized and fully characterized a monosulfonicopillar[5]arene.Subsequently,the host-guest interaction between monosulfonicopillar[5]arene and six alcohols were investigated delicately.Experimental results indicated that monosulfonicopillar[5]arene possessed better binding ability towards alcohol analogs than the dimethoxypillararene and monophosphorylpillararene,especially for butanediol.Monosulfonicopillar[5]arene can be a promising chemosensor for the detection of butanediol.In the second section,we constructed a fluorescence system from the monosulfonicopillar[5]arene and a neutral guest with tetraphenylethene core.The strong fluorescent emission can be observed both in dilute solution and the solid state of the above system.Thus,we fully investigated the causes of fluorescence enhancement and the role of monosulfonicopillar[5]arene played in this fluorescence system.Finally,we utilized this fluorescence system to detect butanediol and ethylenediamine and constructed a temperature sensor with excellent circulation performance.In the third section,we firstly synthesized and fully characterized a water-soluble bissulfonatepillar[5]arene,then we constructed a pH-stable fluorescence system from the bissulfonatepillar[5]arene and a water-soluble tetraphenylethene guest.Subsequently,we researched the fluorescence properties of this host-guest system and applied the as-synthesized fluorescent platform for selective detecting of ferric,the mechanism of selective detecting of ferric was investigated at final.