Abstract
Tetra(4-pyridyl)-cavitand 1 and tetrakis(4-hydroxyphenyl)-cavitand 2 self-assemble into a heterodimeric capsule 1· 2 via four PhOH⋯pyridyl hydrogen bonds in CDCl 3, wherein one molecule of 1,4-disubstituted-benzene as a guest is encapsulated to form a ternary complex, guest@( 1· 2). The X-ray crystallographic analysis of (methyl p-ethoxybenzoate)@( 1· 2) confirmed that the methyl ester and ethoxy groups of the encapsulated guest are oriented to the cavity ends of the 1 and 2 units, respectively. The scope and limitation of guest encapsulation in 1· 2, including guest-binding selectivity and orientational isomeric selectivity, are described from the viewpoint of size complementarity and CH–π, CH–halogen, and halogen–π interactions between guest and the cavity of 1· 2.
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