Synthesis and development of inverse-type nucleoside diarylethene photoswitches

• Verfasst von: Hendrich, Christoph [VerfasserIn]
• Verfasst von: Reinschmidt, Martin [VerfasserIn]
• Verfasst von: Büllmann, Simon [VerfasserIn]
• Verfasst von: Kolmar, Theresa [VerfasserIn]
• Verfasst von: Jäschke, Andres [VerfasserIn]
• Titel: Synthesis and development of inverse-type nucleoside diarylethene photoswitches
• Verf.angabe: Christoph M. Hendrich, Martin Reinschmidt, Simon M. Büllmann, Theresa Kolmar and Andres Jäschke
• E-Jahr: 2024
• Jahr: [11 October 2024]
• Umfang: 9 S.
• Fussnoten: Gesehen am 27.02.2025
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2024
• Band/Heft Quelle: 30(2024), 57, Artikel-ID e202401537, Seite e202401537-1-e202401537-9
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.202401537
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Diarylethenes
• Sach-SW: Inverse-type DAEs
• Sach-SW: Nucleosides
• Sach-SW: Photochromism
• Sach-SW: Photoswitches
• K10plus-PPN: 1918702535

Abstract

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.