Photoresponsive Dissipative Macrocycles Using Visible‐Light‐Switchable Azobenzenes
Esther Nieland, Jona Voss, Andreas Mix, Bernd M. Schmidt
Abstract
Abstract Visible light can be used to shift dynamic covalent imine assemblies out of equilibrium. We studied a fluorinated azobenzene building block that reliably undergoes geometric isomerism upon irradiation. The building block was used in combination with two different amines, ethylenediamine and R,R ‐1,2‐diaminocyclohexane, to create a library of imine macrocycles. Whereas the simple amine can be used to access a polymeric state and a defined bowl‐shaped macrocycle, the chiral amine gives access to a rich network of macrocycles that undergo both isomerisation as well as interconversion between different macrocyclic species, thereby allowing for control over the number of monomers involved in the cyclo‐oligomerization; 1 H‐ and 19 F‐DOSY NMR, MALDI‐MS measurements, and UV/Vis spectroscopy were used to study the processes.