Open AccessSubstituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties
Author(s) -
Felix Klockmann,
Camilla Fangmann,
Elena Zender,
Tobias Schanz,
Claudia Catapano,
Andreas Terfort
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c02524
Subject(s) - azobenzene , methanol , solvent , photochemistry , chemistry , ring (chemistry) , yield (engineering) , combinatorial chemistry , organic chemistry , materials science , molecule , metallurgy
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.