Thermal e / Z Isomerization in First Generation Molecular Motors

Shunsuke Kuwahara; Yuri Suzuki; Naoya Sugita; Mari Ikeda; Fumi Nagatsugi; Nobuyuki Harada; Yoichi Habata

doi:10.1021/acs.joc.7b03264

Thermal e / Z Isomerization in First Generation Molecular Motors

Shunsuke Kuwahara, Yuri Suzuki, Naoya Sugita, Mari Ikeda, Fumi Nagatsugi, Nobuyuki Harada, Yoichi Habata

Division of Organic- and Biomaterials Research

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

8 Citations (Scopus)

Abstract

Determination of a thermal E/Z isomerization barrier of first generation molecular motors is reported. Stable (E)-1a directly converts to stable (Z)-1c without photochemical E/Z isomerization. The activation Gibbs energy of the isomerization was determined to be 123 kJ mol^-1 by circular dichroism spectral changes. Density functional theory calculations show that (Z)-1c is ∼11.4 kJ mol^-1 more stable than (E)-1a.

Original language	English
Pages (from-to)	4800-4804
Number of pages	5
Journal	Journal of Organic Chemistry
Volume	83
Issue number	8
DOIs	https://doi.org/10.1021/acs.joc.7b03264
Publication status	Published - 2018 Apr 20

ASJC Scopus subject areas

Organic Chemistry

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title = "Thermal e / Z Isomerization in First Generation Molecular Motors",

abstract = "Determination of a thermal E/Z isomerization barrier of first generation molecular motors is reported. Stable (E)-1a directly converts to stable (Z)-1c without photochemical E/Z isomerization. The activation Gibbs energy of the isomerization was determined to be 123 kJ mol-1 by circular dichroism spectral changes. Density functional theory calculations show that (Z)-1c is ∼11.4 kJ mol-1 more stable than (E)-1a.",

author = "Shunsuke Kuwahara and Yuri Suzuki and Naoya Sugita and Mari Ikeda and Fumi Nagatsugi and Nobuyuki Harada and Yoichi Habata",

note = "Funding Information: This work was supported by JSPS KAKENHI (Grant nos. JP22750159 and JP17K05845) and the MEXT-Supported Program for the Strategic Research Foundation at Private Universities (2012−2016) for S.K.",

year = "2018",

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doi = "10.1021/acs.joc.7b03264",

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T1 - Thermal e / Z Isomerization in First Generation Molecular Motors

AU - Kuwahara, Shunsuke

AU - Suzuki, Yuri

AU - Sugita, Naoya

AU - Ikeda, Mari

AU - Nagatsugi, Fumi

AU - Harada, Nobuyuki

AU - Habata, Yoichi

N1 - Funding Information: This work was supported by JSPS KAKENHI (Grant nos. JP22750159 and JP17K05845) and the MEXT-Supported Program for the Strategic Research Foundation at Private Universities (2012−2016) for S.K.

PY - 2018/4/20

Y1 - 2018/4/20

N2 - Determination of a thermal E/Z isomerization barrier of first generation molecular motors is reported. Stable (E)-1a directly converts to stable (Z)-1c without photochemical E/Z isomerization. The activation Gibbs energy of the isomerization was determined to be 123 kJ mol-1 by circular dichroism spectral changes. Density functional theory calculations show that (Z)-1c is ∼11.4 kJ mol-1 more stable than (E)-1a.

AB - Determination of a thermal E/Z isomerization barrier of first generation molecular motors is reported. Stable (E)-1a directly converts to stable (Z)-1c without photochemical E/Z isomerization. The activation Gibbs energy of the isomerization was determined to be 123 kJ mol-1 by circular dichroism spectral changes. Density functional theory calculations show that (Z)-1c is ∼11.4 kJ mol-1 more stable than (E)-1a.

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Thermal e / Z Isomerization in First Generation Molecular Motors

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