Reversible heterochiral aggregation/dissociation of bis(2-hydroxyphenyl) diamides driven by UV/Vis irradiation

Akihiro Nojiri; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.201106832

Reversible heterochiral aggregation/dissociation of bis(2-hydroxyphenyl) diamides driven by UV/Vis irradiation

Akihiro Nojiri, Naoya Kumagai, Masakatsu Shibasaki

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

16 Citations (Scopus)

Abstract

Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365-nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422-nm). The precipitation and dissolution is manifestly reversible.

Original language	English
Pages (from-to)	2137-2141
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	51
Issue number	9
DOIs	https://doi.org/10.1002/anie.201106832
Publication status	Published - 2012 Feb 27
Externally published	Yes

Keywords

azobenzene
dynamic aggregation
hydrogen bonds
photochromism
self-assembly

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201106832

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abstract = "Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365-nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422-nm). The precipitation and dissolution is manifestly reversible.",

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author = "Akihiro Nojiri and Naoya Kumagai and Masakatsu Shibasaki",

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AU - Nojiri, Akihiro

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2012/2/27

Y1 - 2012/2/27

N2 - Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365-nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422-nm). The precipitation and dissolution is manifestly reversible.

AB - Light to dissolve: (R)- and (S)-diamides bearing a hydrogen-bonding framework (red in picture) and a trans-azobenzene unit (blue) form an insoluble heterochiral aggregate, which can be dissolved by photoisomerization of the azobenzene unit to the cis conformation by UV irradiation (365-nm). The insoluble aggregate was formed again by subsequent irradiation with visible light (>422-nm). The precipitation and dissolution is manifestly reversible.

KW - azobenzene

KW - dynamic aggregation

KW - hydrogen bonds

KW - photochromism

KW - self-assembly

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JO - Angewandte Chemie - International Edition

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ER -

Reversible heterochiral aggregation/dissociation of bis(2-hydroxyphenyl) diamides driven by UV/Vis irradiation

Abstract

Keywords

ASJC Scopus subject areas

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