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Synthesis and development of inverse-type nucleoside diarylethene photoswitches

Nucleosidic diarylethenes (DAEs) have evolved from an emerging class of photochromes into a well-established option for integrating photochromic functionalities into biological systems. However, a comprehensive understanding of how chemical structure influences their photochromic properties remains...

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Main Authors: Hendrich, Christoph (Author) , Reinschmidt, Martin (Author) , Büllmann, Simon (Author) , Kolmar, Theresa (Author) , Jäschke, Andres (Author)
Format: Article (Journal)
Language:English
Published: [11 October 2024]
In: Chemistry - a European journal
Year: 2024, Volume: 30, Issue: 57, Pages: e202401537-1-e202401537-9
ISSN:1521-3765
DOI:10.1002/chem.202401537
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/chem.202401537
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202401537
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Author Notes:Christoph M. Hendrich, Martin Reinschmidt, Simon M. Büllmann, Theresa Kolmar and Andres Jäschke

MARC

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520 |a Nucleosidic diarylethenes (DAEs) have evolved from an emerging class of photochromes into a well-established option for integrating photochromic functionalities into biological systems. However, a comprehensive understanding of how chemical structure influences their photochromic properties remains essential. While structural features, such as an inverse connection between the aryl residues and the ethene bridge, are well-documented for classical DAEs, their application to nucleosidic DAEs has been underexplored. In this study, we address this gap by developing three distinct types of inverse nucleosidic DAEs-semi-inverse thiophenes, semi-inverse uridines and inverse uridines. We successfully synthesized these compounds and conducted comprehensive analyses of their photostationary states, thermal stability, reversibility, and reaction quantum yields. Additionally, we conducted an in-depth comparison of their photochromic properties with those of their normal-type counterparts. Among the synthesized compounds, seven semi-inverse thiophenes exhibited the most promising characteristics. Notably, these compounds demonstrated excellent fatigue resistance, with up to 96 % retention of photochromic activity over 40 switching cycles, surpassing the performance of all comparable nucleosidic DAEs reported to date. These findings hold significant promise for future applications in various fields. 
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