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Updated: Aug 12, 2026

Synthesis of Information-bearing Peptoids and their Sequence-directed Dynamic Covalent Self-assembly
Published on: February 6, 2020
Orientational isomerism and binding ability of nonsymmetrical guests encapsulated in a self-assembling heterodimeric
Kenji Kobayashi1, Kei Ishii, Masamichi Yamanaka
1Department of Chemistry, Faculty of Science, Shizuoka University, Japan. skkobay@ipc.shizuoka.ac.jp
Abstract:
The ability of a guest to induce the assembly of tetracarboxyl-cavitand 1 and tetra(3-pyridyl)-cavitand 2 into a heterodimeric capsule 12, and the orientational isomerism of nonsymmetrical p-disubstituted-benzene guests encapsulated in 12, are described. For example, the ability of a guest to induce the assembly of guest subset(12) increases in the order p-iodoaniline< or =p-chloroanisole < p-bromoanisole < N-methyl-p-iodoaniline < p-iodoanisole. For these five guests encapsulated in 12, the halogen atoms are specifically oriented with respect to the cavity of the 2 unit. By contrast, the orientational isomeric selectivities of p-chloroiodobenzene, p-bromoiodobenzene, and p-methylanisole encapsulated in 12 are quite low, in the range of 1:1.7 to 1:1. The ortho-fluoro derivatives of these three guests, however, are encapsulated in 12 with a highly selective orientation, in which the substituent next to the fluorine atom greatly prefers the cavity of the 2 unit to that of the 1 unit.
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