Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties

11,12-Dihydrodibenzo[c,g]-1,2-diazocines have been established as a viable alternative to azobenzene for photoswitching, in particular, as they show an inverted switching behavior: the ground state is the Z isomer. In this paper, we present an improved method to obtain dibenzodiazocine and its derivatives from the respective 2-nitrotoluenes in two reaction steps, each proceeding in minutes. This fast access to a variety of derivatives permitted the study of substitution effects on the synthesis and on the photochemical properties. With biochemical applications in mind, methanol was chosen as a protic solvent system for the photochemical investigations. In contrast to the azobenzene system, none of the tested substitution patterns resulted in more efficient switching or in significantly prolonged half-lives, showing that the system is dominated by the ring strain.

Automated summary

11,12-Dihydrodibenzo[c,g]-1,2-diazocines have been identified as an alternative to azobenzene for photoswitching, showing inverted switching behavior. An improved method for synthesis allows for studying substitution effects on photochemical properties, with none resulting in more efficient switching due to ring strain dominance.