A photochemically activated cyclophane

Seiji Shinkai; Akiko Yoshioka; Hatsumi Nakayama; Osamu Manabe

doi:10.1039/P29900001905

A photochemically activated cyclophane

Seiji Shinkai, Akiko Yoshioka, Hatsumi Nakayama, Osamu Manabe

Institute for Advanced Study

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

23 Citations (Scopus)

Abstract

A water-soluble, photoresponsive macrocycle (1), composed of two N ⁺ cations and two azobenzene units, has been synthesized. This cyclophane changes its cavity shape in response to a photoinduced trans-cis isomerization of the azobenzene moieties. The photoresponsive association behaviour has been examined for mono- and di-carboxylate guest molecules through spectral studies, thermal cis→trans isomerization, and electrical conductance measurements. It has been shown that cis-(1) strongly binds guest molecules having a general structure ^-OOC(CH₂) _nCOO^-, the driving force for the guest binding being the electrostatic force between two N⁺ cations and two carboxylate anions and the hydrophobic force between the cis-azobenzene units and a -(CH ₂)_n-chain. The results establish that the guest selectivity in host-guest chemistry can be controlled by the enforced change in the cavity shape.

Original language	English
Pages (from-to)	1905-1909
Number of pages	5
Journal	Journal of the Chemical Society, Perkin Transactions 2
Issue number	11
DOIs	https://doi.org/10.1039/P29900001905
Publication status	Published - Dec 1 1990

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1039/P29900001905

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title = "A photochemically activated cyclophane",

abstract = "A water-soluble, photoresponsive macrocycle (1), composed of two N + cations and two azobenzene units, has been synthesized. This cyclophane changes its cavity shape in response to a photoinduced trans-cis isomerization of the azobenzene moieties. The photoresponsive association behaviour has been examined for mono- and di-carboxylate guest molecules through spectral studies, thermal cis→trans isomerization, and electrical conductance measurements. It has been shown that cis-(1) strongly binds guest molecules having a general structure -OOC(CH2) nCOO-, the driving force for the guest binding being the electrostatic force between two N+ cations and two carboxylate anions and the hydrophobic force between the cis-azobenzene units and a -(CH 2)n-chain. The results establish that the guest selectivity in host-guest chemistry can be controlled by the enforced change in the cavity shape.",

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T1 - A photochemically activated cyclophane

AU - Shinkai, Seiji

AU - Yoshioka, Akiko

AU - Nakayama, Hatsumi

AU - Manabe, Osamu

PY - 1990/12/1

Y1 - 1990/12/1

N2 - A water-soluble, photoresponsive macrocycle (1), composed of two N + cations and two azobenzene units, has been synthesized. This cyclophane changes its cavity shape in response to a photoinduced trans-cis isomerization of the azobenzene moieties. The photoresponsive association behaviour has been examined for mono- and di-carboxylate guest molecules through spectral studies, thermal cis→trans isomerization, and electrical conductance measurements. It has been shown that cis-(1) strongly binds guest molecules having a general structure -OOC(CH2) nCOO-, the driving force for the guest binding being the electrostatic force between two N+ cations and two carboxylate anions and the hydrophobic force between the cis-azobenzene units and a -(CH 2)n-chain. The results establish that the guest selectivity in host-guest chemistry can be controlled by the enforced change in the cavity shape.

AB - A water-soluble, photoresponsive macrocycle (1), composed of two N + cations and two azobenzene units, has been synthesized. This cyclophane changes its cavity shape in response to a photoinduced trans-cis isomerization of the azobenzene moieties. The photoresponsive association behaviour has been examined for mono- and di-carboxylate guest molecules through spectral studies, thermal cis→trans isomerization, and electrical conductance measurements. It has been shown that cis-(1) strongly binds guest molecules having a general structure -OOC(CH2) nCOO-, the driving force for the guest binding being the electrostatic force between two N+ cations and two carboxylate anions and the hydrophobic force between the cis-azobenzene units and a -(CH 2)n-chain. The results establish that the guest selectivity in host-guest chemistry can be controlled by the enforced change in the cavity shape.

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