Department of Chemical Organic Technology and Petrochemistry, Silesian University of Technology, Krzywoustego 4, 44-100Gliwice, Poland.
ACS Sens. 2023 Feb 24;8(2):721-727. doi: 10.1021/acssensors.2c02251. Epub 2023 Jan 25.
Molecular switches have become an area of great interest in recent years. They are explored as high-density data storage and organic diodes in molecular electronics as well as chemosensors due to their ability to undergo a transition between well-defined structures under the action of external stimuli. One of the types of such switches is hydrazones. They work by changing the configuration from E to Z under the influence of pH or light. The change in configuration is accompanied by a change in the absorption band and changes in the nuclear magnetic resonance (NMR) spectrum. In this publication, the structure-property relationship of fluorinated hydrazone switches was established. A linear relationship between the Hammett substituent constants and the pH where the switching occurs was found. Introduction of strong electron-donating groups allowed obtaining a hydrazone switch of p = 6 suitable for application in F MRI as contrast agents.
近年来,分子开关已经成为一个非常热门的研究领域。由于它们在外来刺激的作用下能够在明确定义的结构之间进行转换,因此它们被探索用于高密度数据存储和分子电子学中的有机二极管以及化学传感器。这类开关之一是腙。在 pH 值或光的影响下,它们通过改变构型从 E 变为 Z 来工作。构型的变化伴随着吸收带的变化和核磁共振(NMR)谱的变化。在本出版物中,建立了氟化腙开关的结构-性质关系。发现了取代基常数与发生开关的 pH 值之间的线性关系。引入强供电子基团可以得到 p = 6 的腙开关,适用于作为 F MRI 中的造影剂。
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