Synthesis of N-acetyl diazocine derivatives via cross-coupling reaction
Thomas Brandt, Pascal Lentes, Jeremy Rudtke, Michael Hösgen, Christian Näther, Rainer Herges
TL;DR
Researchers synthesized new water-soluble diazocine derivatives using cross-coupling reactions, improving their performance in aqueous environments.
Contribution
A novel synthesis strategy for water-soluble diazocine derivatives using cross-coupling reactions is introduced.
Findings
Fourteen substituted diazocine derivatives were successfully synthesized via Stille, Suzuki, and Buchwald–Hartwig reactions.
X-ray structures confirmed the structures of derivatives 1, 2, and 7.
The modified diazocines maintain high switching efficiency even in aqueous solutions.
Abstract
Diazocines are photoswitches derived from azobenzenes by bridging the two phenyl rings in ortho position with a CH2CH2 group forming an eight membered (diazocine) ring. Diazocine is superior to most azobenzenes in almost all photophysical properties (switching efficiency, quantum yield, wavelengths etc.). The biggest advantage, especially in photopharmacology and when used in photoswitchable materials, is the inverted thermodynamic stability of the two switching states (isomers). The Z isomer is more stable than the E form. However, one disadvantage that it shares with the frequently used azobenzene is that the switching efficiency decreases sharply with increasing water content in the solvent. In a recently published paper, we reported that replacing one CH2 group in the bridge with NCOCH3 not only confers intrinsic water solubility, but also largely eliminates the problem of reduced…
Genes, proteins, chemicals, diseases, species, mutations and cell lines named across the full text — each resolved to its canonical identifier and authoritative record.
Click any figure to enlarge with its caption.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14
Figure 15
Figure 16
Figure 17
Figure 18
Figure 19
Figure 20
Figure 21
Figure 22
Figure 23
Figure 24
Figure 25
Figure 26
Figure 27
Figure 28
Figure 29
Figure 30
Figure 31
Figure 32
Figure 33
Figure 34
Figure 35Peer Reviews
No public reviews on file for this paper yet. If you reviewed it on a platform where reviews are public (OpenReview, ICLR, NeurIPS, ICML), you can paste yours below so the community can read it here.
Videos
No videos yet. Explain this paper in a talk, walkthrough, or lecture? Add one.
Taxonomy
TopicsPhotochromic and Fluorescence Chemistry · Chemical synthesis and alkaloids · Axial and Atropisomeric Chirality Synthesis