Water-soluble pillar[4]arene[1]quinone: Synthesis,host-guest property and application in the fluorescence turn-on sensing of ethylenediamine in aqueous solution,organic solvent and air

Water-soluble pillar5]arenes are a class of typical macrocycles and have aroused tremendous attention for its easy to modify, abundant host-guest properties and extensive applications. However, up to now, all the reported water-soluble pillar5]arenes acted as the host molecules, whereas they failed to be postsynthetically modified, which seriously impeded the development of the pillar5]arene-based supramolecular chemistry. In this work, a new water-soluble pillar5]arene, pillar4]arene1]quinone, was designed and synthsized with eight quaternary ammonium groups as well as a quinone units. Such a new water-soluble pillar4]arene1]quinone was capable of forming 1:1 stable complex with sodium 1-octanesulfonate in aqueous solution. Since the 1,4-quinone unit of WP4]Q1] could react with ethylenediamine (EDA) to form a conjugated quinoxaline structure, so pillar4]arene1]quinone could apply to the facile fluorescence turn-on sensing of EDA in aqueous solution, organic solvent and air.