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CC BY 4.0 · Synlett 2025; 36(11): 1569-1573
DOI: 10.1055/a-2567-1399
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Supramolecular Catalysis and Molecular Switches

2,8-Dihalogenated Diazocines: Versatile Reactants for Functionalized Photoswitches

Maximilian J. Notheis  ‡
,
Vigan Sahiti  ‡
,
Vivienne Prangenberg
,
Johannes S. Kruse
,
Larissa K. S. von Krbek  ∗

This work was supported by the Fonds der Chemischen Industrie (Liebig Fellowship) and the German Research Foundation (DFG; Emmy Noether Programme, 446317932). M.J.N. and V.S. thank the FCI and Avicenna-Studienwerk, respectively, for their Ph.D. scholarships.
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Abstract

Diazocine photoswitches possess distinctive structural characteristics and remarkable photochemical properties, leading to their growing application in photopharmacology and smart materials. We report the synthesis of 2,8-pseudo-para-substituted diazocines with two bromo, two iodo, or a combination of both substituents, achieving effective scalability. Besides demonstrating good reactivity in Suzuki cross-coupling reactions, the substituted diazocines predominantly retain their good photochemical properties, rendering them valuable components for said applications.

Key words

photoswitches - diazocines - cross-coupling - gram-scale synthesis - photophysical properties

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-2567-1399.
  • Supporting Information


Publication History

Received: 25 February 2025

Accepted after revision: 21 March 2025

Accepted Manuscript online:
26 March 2025

Article published online:
12 May 2025

© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)

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