Separation and detection of meta‐ and ortho‐ substituted benzene isomers by water‐soluble pillar[5]arene

G. Zhang, B. Moosa, A. Chen, N. Khashab
ChemPlusChem, 10.1002/cplu.202000275, (2020)


Intrinsic Porosity, Pillararene, Molecular recognition, Host-guest chemistry, Isomer separation


​Efficient and energy‐saving separation of benzene isomers bearing a diverse range of functional groups is a world‐changing challenge due to their overlapping physicochemical properties. Here, we report a water soluble pillar[5]arene ( WP5 ) that is successfully used as a multi‐functional material for the separation and detection of meta/ortho‐ substituted benzene isomers in water. A liquid‐liquid extraction strategy was used for the separation of these benzene isomers based on their different affinity to WP5 in water. This showed more than 88% separation preference for binding meta‐xylene ( MX ) over ortho‐xylene ( OX ) in the intrinsic pore of WP5 , under ambient conditions. Furthermore, a fluorescence indicator system based on WP5 and a fluorescent dye molecule (10‐methylacridinium, D ) was adopted and exhibited significant fluorescence and optical discrimination upon the addition of MX compared to OX , which implies that a simple proper detection can be performed prior to engaging in the separation process.



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