Organic Chemistry Frontiers: Functional group introduction and aromatic unit variation

... in a set of π-conjugated macrocycles. Previously posted on ChemRxiv, this article is now accepted for publication in Organic Chemistry Frontiers. In the article, we reveal the central role of local and global aromaticity for rationalizing the properties of a set of π-conjugated macrocycles.


We are delighted that the article will be part of a special issue on Macrocycle-based Supramolecular Elements, edited by Prof. Frank Würthner (University of Würzburg), who published an essay on A Periodic System of Supramolecular Elements last year.



π-Conjugated macrocycles are molecules with unique properties that are increasingly exploited for applications and the question of whether they can sustain global aromatic or antiaromatic ring currents is particularly intriguing. However, there are only a small number of experimental studies that investigate how the properties of π‑conjugated macrocycles evolve with systematic structural changes. In our preprint, we present such a systematic experimental study of a set of [2.2.2.2]cyclophanetetraenes, all with formally Hückel antiaromatic ground states, and combine it with an in-depth computational analysis.


The study contributes to the development of structure–property relationships and molecular design guidelines and will help to understand, rationalize, and predict the properties of other π‑conjugated macrocycles. It will also assist in the design of macrocycle-based supramolecular elements with defined properties.


Congratulations to Martina for her great work on the synthesis of the macrocycles and a huge thanks to all our collaborators on this work!


M. Rimmele, W. Nogala, M. Seif-Eddine, M. M. Roessler, M. Heeney, F. Plasser,* F. Glöcklhofer,* Functional group introduction and aromatic unit variation in a set of π-conjugated macrocycles: revealing the central role of local and global aromaticity, Org. Chem. Front. 2021, accepted manuscript, DOI:10.1039/D1QO00901J. [Link, open access] [Preprint link, open access]