Nitrogen Bridged Diazocines: Photochromes Switching within the Near-Infrared Region with High Quantum Yields in Organic Solvents and in Water

Pascal Lentes, Eduard Stadler, Fynn Röhricht, Arne Brahms, Jens Gröbner, Frank D. Sönnichsen, Georg Gescheidt, Rainer Herges

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Diazocines are bridged azobenzenes with superior photophysical properties. In contrast to azobenzenes the Z configuration is thermodynamically stable and the E isomer is metastable. We present a new class of nitrogen bridged diazocines with bathochromically shifted switching wavelengths and remarkably high quantum yields (-NH-CH2- bridged diazocine: φZ→E = 0.57, φE→Z = 0.8). Z to E isomerization is induced by irradiation with blue light, whereas switching back to the Z isomer is accomplished with light in the near-infrared window (up to 740 nm), which is important for medical applications like photopharmacology (deep tissue penetration). Furthermore, substitution at the bridging nitrogen should provide access to widely applicable tricyclic, photoswitchable pharmacophores. The -NAc-CH2- bridged derivative is soluble in water, and all photophysical properties (conversion rates, quantum yields, and thermal half-lives) are largely retained. Hence, this diazocine is an ideal photoswitch for applications in biochemical systems and in photopharmacology.

Original languageEnglish
Pages (from-to)13592-13600
Number of pages9
JournalJournal of the American Chemical Society
Volume141
Issue number34
DOIs
Publication statusPublished - 28 Aug 2019

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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