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

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

25 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 - 1990
Externally published	Yes

All Science Journal Classification (ASJC) codes

General Chemistry

Access to Document

10.1039/P29900001905

Cite this

@article{4455930b546e4596bb3eaae34e9834c3,

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.",

author = "Seiji Shinkai and Akiko Yoshioka and Hatsumi Nakayama and Osamu Manabe",

year = "1990",

doi = "10.1039/P29900001905",

language = "English",

pages = "1905--1909",

journal = "Journal of the Chemical Society, Perkin Transactions 2",

issn = "1472-779X",

publisher = "Royal Society of Chemistry",

number = "11",

}

TY - JOUR

T1 - A photochemically activated cyclophane

AU - Shinkai, Seiji

AU - Yoshioka, Akiko

AU - Nakayama, Hatsumi

AU - Manabe, Osamu

PY - 1990

Y1 - 1990

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.

UR - https://www.scopus.com/pages/publications/37049078447

UR - https://www.scopus.com/pages/publications/37049078447#tab=citedBy

U2 - 10.1039/P29900001905

DO - 10.1039/P29900001905

M3 - Article

AN - SCOPUS:37049078447

SN - 1472-779X

SP - 1905

EP - 1909

JO - Journal of the Chemical Society, Perkin Transactions 2

JF - Journal of the Chemical Society, Perkin Transactions 2

IS - 11

ER -

A photochemically activated cyclophane

Abstract

All Science Journal Classification (ASJC) codes

Access to Document

Other files and links

Fingerprint

Cite this