Carbon-carbon double bond in pillar[5]arene cavity: Selective binding of cis/trans-olefin isomers

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The binding behavior of pillar[5]arenes (P5As) towards a series of olefin guests ((E)-1,4-dichlorobut-2-ene(1E), (Z)-1,4-dichlorobut-2-ene (1Z), (E)-but-2-ene-1,4-diol (2E), and (Z)-but-2-ene-1,4-diol (2Z), as well as an alkyne derivative l,4-dichlorobut-2-yne (3)) have been studied in organic solution. P5As exhibit considerable selectivities for the trans-olefin isomers (1E and 2E) over their cis-isomers (1Z and 2Z). The cis/trans-selective interactions hold the potential of utilizing P5As to separate olefin isomers.
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