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Fluorine-Substituted Molecular Motors with a Quaternary Stereogenic Center

机译：氟取代的分子电机，季型立体中心

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摘要

A series of unprecedented second generation molecular motors featuring a quaternary stereogenic center substituted with a fluorine atom has been synthesized. It is demonstrated that a seemingly benign replacement of the stereogenic hydrogen for a fluorine atom, regarded as a common substituent in pharmacology, resulted in a dramatic change in the energetic profile of thermal helix inversion. The barrier for the thermal helix inversion was found to increase considerably (by 20–30 kJmol~(-1)), presumably due to destabilization of the transition state by increased steric hindrance when the fluorine atom is forced to pass over the lower half of the motor. This results in the activation barrier for the thermal helix inversion to be higher than the barrier for backward thermal E–Z isomerization, impairing the motor function. A fluorine-substituted motor capable of performing unidirectional rotation is successfully prepared when these limitations are considered in the design phase.
机译：已经合成了一系列前所未有的第二代第二代分子电机，其具有由氟原子取代的季静根中心。 结果表明，在药理学中常见的氟原子的似乎良换的氟原子替代，导致热螺旋反转的热量剖面中的剧烈变化。 发现热螺旋反转的屏障显着增加（通过20-30kjmol〜（-1）），可能是由于在氟原子被迫通过下半部的氟原子时通过增加的空间阻断而导致过渡状态的破坏性障碍 电机。 这导致热螺旋反转的激活屏障高于向后热E-Z异构化的屏障，损害电动机功能。 当在设计阶段考虑这些限制时，成功地制备了能够进行单向旋转的氟取代的电动机。

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  • 来源
    《Chemistry: A European journal》 |2017年第27期|共11页
  • 作者

    Peter ?tacko; Jos C. M. Kistemaker; Ben L. Feringa;

  • 作者单位

    Centre for Systems Chemistry Stratingh Institute for Chemistry University of Groningen Nijenborgh 4 9747 AG Groningen (The Netherlands) Fax: (+31) 50-363-4296;

    Centre for Systems Chemistry Stratingh Institute for Chemistry University of Groningen Nijenborgh 4 9747 AG Groningen (The Netherlands) Fax: (+31) 50-363-4296;

    Centre for Systems Chemistry Stratingh Institute for Chemistry University of Groningen Nijenborgh 4 9747 AG Groningen (The Netherlands) Fax: (+31) 50-363-4296;

  • 收录信息
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 应用化学;
  • 关键词

    fluorine; molecular motor; photoisomerization; quaternary; unidirectional;

    机译：氟;分子电机;光象化;第四纪;单向;

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