biostudies-literatureNieland EDeutsche Forschungsgemeinschafte202212745https://www.ebi.ac.uk/biostudies/studies/S-EPMC9828355biostudies-literatureUnknown61(48)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.Angewandte Chemie (International ed. in English)Photoresponsive Dissipative Macrocycles Using Visible-Light-Switchable Azobenzenes.PMC9828355417919780INST 208/740-1 FUGGSCHM 3101/5-1Voss JMix ANieland ESchmidt BMfalsePhotoresponsive Dissipative Macrocycles Using Visible-Light-Switchable Azobenzenes.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.2022-01-01T00:00:00Z2022 Nov2026-03-18T13:51:18.365Z2025-04-04T09:30:33.919ZS-EPMC98283553616524010.1002/anie.202212745