Paracyclophanetetraene (PCT) and its derivatives are prime examples of macrocycles with concealed antiaromaticity. However, further exploration of PCTs has been hindered by the lack of halogenated molecular building blocks that would permit their integration into larger conjugated molecules by cross-coupling reactions. In our article published in MSDE, we present two dibrominated PCTs, obtained as a mixture of regioisomers from a three-step synthesis, and demonstrate their functionalisation via Suzuki cross-coupling reactions. Optical, electrochemical, and theoretical studies reveal that aryl substituents can subtly tune the properties and behaviour of PCT, showing that this is a viable strategy in further exploring this promising class of materials.
The article is part of MSDE's Emerging Investigator Series, showcasing the work being conducted by Emerging Investigators in all areas of molecular engineering across the globe. The series is meant to highlight up-and-coming scientists, who have been identified as having the potential to influence future directions in the field. We thank MSDE for the invitation and opportunity to contribute to this series!
T. L. R. Bennett, A. V. Marsh, J. M. Turner, F. Plasser, M. Heeney, F. Glöcklhofer,* Functionalisation of conjugated macrocycles with type I and II concealed antiaromaticity via cross-coupling reactions, Mol. Syst. Des. Eng. 2023, advance article, DOI:10.1039/d3me00045a. [Link, open access] Part of the Emerging Investigator Series.