Substituted Nitrogen-Bridged Diazocines

  1. Pascal Lentes,
  2. Jeremy RudtkeORCID Logo and
  3. Rainer HergesORCID Logo

Submitting author affiliation: Universität Kiel, Kiel, Germany

Beilstein Arch. 2021, 202116. https://doi.org/10.3762/bxiv.2021.16.v1

Published 08 Mar 2021

  • Preprint

Abstract

Novel nitrogen bridged diazocines (triazocines) were synthesized that carry a formyl or an acetyl group at the CH2NR- bridge and bromo- or iodo substituents at the distant phenyl ring. The photophysical properties were investigated in acetonitrile and water. As compared to previous approaches the yields of the intramolecular azo cyclizations were increased (from ~40 to 60%) by an oxidative approach starting from the corresponding aniline precursors. The ZE photoconversion yields in acetonitrile are 80-85% and the thermal half-lives of the metastable E configurations are 31-74 min. Particularly, the high photoconversion yields (~70%) of the water-soluble diazocines are noteworthy, which makes them promising candidates for applications in photopharmacology. The halogen substituents allow further functionalization via cross-coupling reactions.

Keywords: photoswitch; visible light switch; diazocine; triazocine; water-soluble switch; photopharmacology, bridged azobenzene

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Lentes, P.; Rudtke, J.; Herges, R. Beilstein Arch. 2021, 202116. doi:10.3762/bxiv.2021.16.v1

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