Ion Pair-Driven Heterodimeric Capsule Based on Boronate Esterification: Construction and the Dynamic Behavior

J. Am. Chem. Soc., 129 (49), 15126 -15127, 2007. 10.1021/ja076792f S0002-7863(07)06792-3
Web Release Date: November 16, 2007

Ion Pair-Driven Heterodimeric Capsule Based on Boronate Esterification: Construction and the Dynamic Behavior

Kenichi Kataoka, Tony D. James, and Yuji Kubo*

Department of Applied Chemistry, Graduate School of Science and Technology, Saitama University, 255 Shimo-ohkubo, Sakura-ku, Saitama 338-8570, Japan, and Department of Chemistry, University of Bath, Bath, BA2 7AY, U.K.

yuji@apc.saitama-u.ac.jp

Received September 8, 2007

Abstract:

We describe the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix[3]arene 2. Although 1 does not interact with 2 in a protic solution, in the presence of Et₄NAcO quantitative formation of a heterodimeric capsule via boronate esterification was observed in the NMR, a direct result of anion-induced boronate ester formation and the Et₄N⁺ template. Reversible boronate esterification allowed us to selectively control capsule assembly using pH switching.

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