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

Kenichi Kataoka; Tony D James; Yuji Kubo

doi:10.1021/ja076792f

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

Kenichi Kataoka, Tony D James, Yuji Kubo

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

90 Citations (SciVal)

Abstract

We describe the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix[3]arene 2. Although I 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.

Original language	English
Pages (from-to)	15126-15127
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	49
DOIs	https://doi.org/10.1021/ja076792f
Publication status	Published - 2007

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abstract = "We describe the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix[3]arene 2. Although I 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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AU - Kubo, Yuji

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N2 - We describe the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix[3]arene 2. Although I 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.

AB - We describe the ion pair-driven heterodimeric capsule formation of a cyclotricatechylene 1 and a boronic acid-appended hexahomotrioxacalix[3]arene 2. Although I 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.

UR - http://dx.doi.org/10.1021/ja076792f

U2 - 10.1021/ja076792f

DO - 10.1021/ja076792f

M3 - Article

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 49

ER -

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

Abstract

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