Tomas Solomek

Journal of the American Chemical Society The strain of a carbon nanohoop is used to transform photochemically inert ferrocene into an efficient iron photocage activatable with benign green light. View the article.

JACS cover of our work from January is out today. Enjoy the design by @pstacko.bsky.social👍🏻 pubs.acs.org/toc/jacsat/1...

Short account about the story from Harm Ikink @uva.nl: hims.uva.nl/content/news...

🙏🏻 again to the team, Remek Krecijasz, Juraj Malincik, Matthew Simon, and 💰 by @erc.europa.eu

Kinetic Trapping of Rylene Diimide Covalent Organic Cages Formation of imine organic cages relies on the error correction of dynamic covalent chemistry. Here, we demonstrate kinetically trapped rylene diimide [2 + 3] cages formed in high yields, and we investigate the effect of substituents on their formation kinetics and stability. Thereby, we identified that alkoxy groups in 2,4,6-trialkoxy-1,3,5-triformylbenzene, which are used to stabilize covalent organic cages or COFs, act as stereoelectronic chameleons. They increase the electrophilicity of the tritopic aldehyde and the rate of the imine bond formation but simultaneously diminish its kinetic stability in solution. We also show that aldehydes present in the solution may have a detrimental effect on the cage’s kinetic stability. In addition, we observed [2 + 2] macrocycles as intermediates in the cage formation and decomposition. We propose that these intermediates represent interesting targets to explore the threshold at which an imine assembly with a rung structure may turn from thermodynamic to kinetic control. Generally, this work underscores critical factors governing the chemistry of kinetically trapped imine assemblies, such as steric bulk, (stereo)electronics, presence of catalysts, and water concentration.

Here we go! My first post on a new social platform. I somehow feel old doing this🫣 Nevertheless, there are things to be proud of and those are my students and collaborators🤗 Happy to share the new piece from Sergey Fisher (soon Dr.) in JOC. 🙏🏻 @erc.europa.eu, @uva.nl

pubs.acs.org/doi/10.1021/...