Substituted nitrogen-bridged diazocines

Novel nitrogen-bridged diazocines (triazocines) were synthesized that carry a formyl or an acetyl group at the CH 2 NR-bridge and bromo- iodo-substituents distant phenyl ring. The photophysical properties investigated in acetonitrile water. As compared to previous approaches yields of intramolecular azo cyclizations increased (from ≈40 60%) using oxidative approach starting from corresponding aniline precursors. Z → E photoconversion are 80–85% thermal half-lives metastable configurations 31–74 min. Particularly, high (≈70%) water-soluble noteworthy, which makes them promising candidates for applications photopharmacology. halogen substituents allow further functionalization via cross-coupling reactions.