LAUSR

The compound (–)-(2R,3R)-2,3-dimethoxy-1,1,4,4-tetraphenylbutane-1,4-diol (DMT) forms 2 : 1 host : guest complexes with aniline, N-methylaniline, and N,N-dimethylaniline when recrystallized from these solvents. When the guests competed, as in binary and ternary mixtures, DMT proved to be remarkably selective for the alkylated guests, discriminating consistently against aniline. A host selectivity order of aniline << N-methylaniline < N,N-dimethylaniline was observed. Results from single-crystal diffraction, Hirshfeld surface, and thermal analyses were used to explain the observed preference order. This investigation shows that using the realm of supramolecular chemistry may have future application in the separation of these anilines.