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Metal-binding hydrazone photoswitches for visible light reactivity and variable relaxation kinetics

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Abstract

The range of applications for photoswitching moieties is diverse, and the ability to design switches with variable photochemical and physical properties is consequently important for realizing their potential. Previously we reported on the photochromism of (E)-N′-(1-(2-hydroxyphenyl)ethylidene)isonicotinohydrazide (HAPI), an aroylhydrazone compound first developed as a transition metal chelator. Herein we report the synthesis of structurally related aroylhydrazone chelators and explore the effect of these modifications on their UVA, UVC and blue light photoreactivity, photostationary state composition, photoisomer thermal stability, and relative iron(iii) binding affinity. These findings will inform the next generation of aroylhydrazone photoswitches for metal-gated photoswitching applications.

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Acknowledgments

We thank the National Science Foundation for supporting aspects of this work (CHE-1152054). K. C. H appreciates the US Department of Education GAANN Fellowship (P200A150114). A. T. F. appreciates a Burroughs Wellcome Fellowship from the Department of Chemistry, Duke University. R. C. M. appreciates NSF-REU funding for summer research at Duke (NSF-CHE-1062607). M. S. W. appreciates summer research funding from Department of Chemistry, Duke University. We thank Dr George Dubay and Chris Jernigan for assistance with LC-MS data collection.

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  1. Department of Chemistry, Duke University, Durham, North Carolina, 27708, USA

    Kacey C. Hall, Andrew T. Franks, Rory C. McAtee, Michael S. Wang, Vivian I. Lu & Katherine J. Franz

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  1. Kacey C. Hall
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Correspondence to Katherine J. Franz.

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Hall, K.C., Franks, A.T., McAtee, R.C. et al. Metal-binding hydrazone photoswitches for visible light reactivity and variable relaxation kinetics. Photochem Photobiol Sci 16, 1604–1612 (2017). https://doi.org/10.1039/c7pp00173h

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