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.
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