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Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties.

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.

SUBMITTER: Klockmann F

PROVIDER: S-EPMC8296553 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Substituted Dibenzodiazocines: Rapid Synthesis and Photochemical Properties.

Klockmann Felix F Fangmann Camilla C Zender Elena E Schanz Tobias T Catapano Claudia C Terfort Andreas A

ACS omega 20210708 28

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 effe ...[more]

PMID: 34308074

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