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.

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Author:Felix Klockmann, Camilla Fangmann, Elena Zender, Tobias Schanz, Claudia Catapano, Andreas TerfortORCiDGND
Parent Title (English):ACS omega
Publisher:ACS Publications
Place of publication:Washington DC
Document Type:Article
Date of Publication (online):2021/07/08
Date of first Publication:2021/07/08
Publishing Institution:Universit├Ątsbibliothek Johann Christian Senckenberg
Release Date:2021/08/03
Tag:Azobenzene; Molecular structure; Reaction products; Solvents; Substituents
Page Number:8
First Page:18434
Last Page:18441
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Open-Access-Publikationsfonds:Biochemie, Chemie und Pharmazie
Licence (German):License LogoCreative Commons - Namensnennung 4.0