Tuning the pH of Activation of Fluorinated Hydrazone-Based SwitchesA Pathway to Versatile 19F Magnetic Resonance Imaging Contrast Agents

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 stimu...

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Bibliographic Details
Published in:ACS sensors 2023-02, Vol.8 (2), p.721-727
Main Authors: Janasik, Dawid, Imielska, Patrycja, Krawczyk, Tomasz
Format: Article
Language:English
Online Access:Get full text
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Summary: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 pK a = 6 suitable for application in 19F MRI as contrast agents.
ISSN:2379-3694
2379-3694
DOI:10.1021/acssensors.2c02251