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 |
|---|---|
| URN: | urn:nbn:de:hebis:30:3-618079 |
| DOI: | https://doi.org/10.1021/acsomega.1c02524 |
| ISSN: | 2470-1343 |
| Parent Title (English): | ACS omega |
| Publisher: | ACS Publications |
| Place of publication: | Washington DC |
| Document Type: | Article |
| Language: | English |
| Date of Publication (online): | 2021/07/08 |
| Date of first Publication: | 2021/07/08 |
| Publishing Institution: | Universitätsbibliothek Johann Christian Senckenberg |
| Release Date: | 2021/08/03 |
| Tag: | Azobenzene; Molecular structure; Reaction products; Solvents; Substituents |
| Volume: | 6 |
| Page Number: | 8 |
| First Page: | 18434 |
| Last Page: | 18441 |
| HeBIS-PPN: | 488985013 |
| Institutes: | Biochemie, Chemie und Pharmazie / Biochemie und Chemie |
| Dewey Decimal Classification: | 5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften |
| Sammlungen: | Universitätspublikationen |
| Open-Access-Publikationsfonds: | Biochemie, Chemie und Pharmazie |
| Licence (German): |  Creative Commons - Namensnennung 4.0 |
