Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

Christopher R. Opie; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/anie.201610279

Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

Christopher R. Opie, Naoya Kumagai, Masakatsu Shibasaki

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

10 Citations (Scopus)

Abstract

A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.

Original language	English
Pages (from-to)	3349-3353
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	56
Issue number	12
DOIs	https://doi.org/10.1002/anie.201610279
Publication status	Published - 2017 Mar 13
Externally published	Yes

Keywords

azo compounds
foldamers
helical structures
hydrogen bonds
photochromism

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201610279

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title = "Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding",

abstract = "A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.",

keywords = "azo compounds, foldamers, helical structures, hydrogen bonds, photochromism",

author = "Opie, {Christopher R.} and Naoya Kumagai and Masakatsu Shibasaki",

note = "Funding Information: This work was financially supported by KAKENHI (No. 25713002, 26670009) from JSPS (to N.K.). Dr. Ryuichi Sawa, Yumiko Kubota, and Dr. Kiyoko Iijima are gratefully acknowledged for their assistance with the NMR analysis. We acknowledge Dr. Hidetoshi Noda for assistance with the MD simulations. We would like to thank anonymous reviewers for insightful suggestions which helped to improve the paper. Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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month = mar,

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doi = "10.1002/anie.201610279",

language = "English",

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journal = "Angewandte Chemie - International Edition",

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T1 - Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

AU - Opie, Christopher R.

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

N1 - Funding Information: This work was financially supported by KAKENHI (No. 25713002, 26670009) from JSPS (to N.K.). Dr. Ryuichi Sawa, Yumiko Kubota, and Dr. Kiyoko Iijima are gratefully acknowledged for their assistance with the NMR analysis. We acknowledge Dr. Hidetoshi Noda for assistance with the MD simulations. We would like to thank anonymous reviewers for insightful suggestions which helped to improve the paper. Publisher Copyright: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2017/3/13

Y1 - 2017/3/13

N2 - A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.

AB - A linear molecular architecture equipped with complementary three-fold hydrogen-bonding units embedded with a photoswitchable trans-tetrafluoroazobenzene moiety was synthesized. The transto cis photoisomerism of the azobenzene unit induced drastic changes in the molecular architecture as a result of intramolecular hydrogen bonding as evidenced by NMR spectroscopy and size exclusion chromatography. A minute stereogenic element in the linear trans state enabled stereoselective folding into the cis state, thus producing a globular architecture with enhanced chiroptical property.

KW - azo compounds

KW - foldamers

KW - helical structures

KW - hydrogen bonds

KW - photochromism

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JO - Angewandte Chemie - International Edition

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ER -

Reversible Stereoselective Folding/Unfolding Fueled by the Interplay of Photoisomerism and Hydrogen Bonding

Abstract

Keywords

ASJC Scopus subject areas

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