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Published on: June 10, 2021
Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties
Felix Klockmann1, Camilla Fangmann1, Elena Zender1
1Institute of Inorganic and Analytical Chemistry, University of Frankfurt, Max-von-Laue-Straße 7, 60438 Frankfurt, Germany.
Abstract:
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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