TY  - JOUR
A1  - Klockmann, Felix
A1  - Fangmann, Camilla
A1  - Zender, Elena
A1  - Schanz, Tobias
A1  - Catapano, Claudia
A1  - Terfort, Andreas
T1  - Substituted dibenzodiazocines: rapid synthesis and photochemical properties
T2  - ACS omega
N2  - 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.
KW  - Azobenzene
KW  - Reaction products
KW  - Substituents
KW  - Solvents
KW  - Molecular structure
Y1  - 2021
UR  - http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/61807
UR  - https://nbn-resolving.org/urn:nbn:de:hebis:30:3-618079
SN  - 2470-1343
VL  - 6
SP  - 18434
EP  - 18441
PB  - ACS Publications
CY  - Washington DC
ER  -