Photoswitching of Diazocines in Aqueous Media

Pascal Lentes; Philipp Fruhwirt; Hilde Freimuth; Widukind Moormann; Fabian Kruse; Georg Gescheidt; Rainer Herges

doi:10.1021/acs.joc.1c00065

Photoswitching of Diazocines in Aqueous Media

Pascal Lentes, Philipp Fruhwirt, Hilde Freimuth, Widukind Moormann, Fabian Kruse, Georg Gescheidt, Rainer Herges^*

^*Corresponding author for this work

Institute of Physical and Theoretical Chemistry (6350)

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

Abstract

We present a systematic investigation of the photophysical properties of diazocines in aqueous media. The Z-E photoconversion yields of CH2CH2- and CH2S-bridged diazocines decrease with increasing water content in acetonitrile. However, there is one exception. A CH2-NAc-bridged diazocine mostly retains its photostationary state in water (85 to 72%) because of the high quantum yields for the Z → E conversion. Moreover, it is water-soluble without further substitution and is therefore ideally suited as a photoswitch in biological (aqueous) environments.

Original language	English
Pages (from-to)	4355-4360
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	86
Issue number	5
DOIs	https://doi.org/10.1021/acs.joc.1c00065
Publication status	Published - 5 Mar 2021

ASJC Scopus subject areas

Organic Chemistry

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10.1021/acs.joc.1c00065

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title = "Photoswitching of Diazocines in Aqueous Media",

abstract = "We present a systematic investigation of the photophysical properties of diazocines in aqueous media. The Z-E photoconversion yields of CH2CH2- and CH2S-bridged diazocines decrease with increasing water content in acetonitrile. However, there is one exception. A CH2-NAc-bridged diazocine mostly retains its photostationary state in water (85 to 72%) because of the high quantum yields for the Z → E conversion. Moreover, it is water-soluble without further substitution and is therefore ideally suited as a photoswitch in biological (aqueous) environments. ",

author = "Pascal Lentes and Philipp Fruhwirt and Hilde Freimuth and Widukind Moormann and Fabian Kruse and Georg Gescheidt and Rainer Herges",

note = "Funding Information: The authors gratefully acknowledge financial support by the Deutsche Forschungsgesellschaft (DFG) within the Collaborative Research Center SFB 677, “Function by Switching” and to NAWI Graz. The authors thank Dr. Eduard Stadler for his assistance with the quantum yield measurements. Publisher Copyright: {\textcopyright} ",

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AU - Lentes, Pascal

AU - Fruhwirt, Philipp

AU - Freimuth, Hilde

AU - Moormann, Widukind

AU - Kruse, Fabian

AU - Gescheidt, Georg

AU - Herges, Rainer

N1 - Funding Information: The authors gratefully acknowledge financial support by the Deutsche Forschungsgesellschaft (DFG) within the Collaborative Research Center SFB 677, “Function by Switching” and to NAWI Graz. The authors thank Dr. Eduard Stadler for his assistance with the quantum yield measurements. Publisher Copyright: ©

PY - 2021/3/5

Y1 - 2021/3/5

N2 - We present a systematic investigation of the photophysical properties of diazocines in aqueous media. The Z-E photoconversion yields of CH2CH2- and CH2S-bridged diazocines decrease with increasing water content in acetonitrile. However, there is one exception. A CH2-NAc-bridged diazocine mostly retains its photostationary state in water (85 to 72%) because of the high quantum yields for the Z → E conversion. Moreover, it is water-soluble without further substitution and is therefore ideally suited as a photoswitch in biological (aqueous) environments.

AB - We present a systematic investigation of the photophysical properties of diazocines in aqueous media. The Z-E photoconversion yields of CH2CH2- and CH2S-bridged diazocines decrease with increasing water content in acetonitrile. However, there is one exception. A CH2-NAc-bridged diazocine mostly retains its photostationary state in water (85 to 72%) because of the high quantum yields for the Z → E conversion. Moreover, it is water-soluble without further substitution and is therefore ideally suited as a photoswitch in biological (aqueous) environments.

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JO - Journal of Organic Chemistry

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Photoswitching of Diazocines in Aqueous Media

Abstract

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