Preprint: Functional Group Introduction and Aromatic Unit Variation in π-Conjugated Macrocycles

Our preprint revealing the central role of local and global aromaticity for rationalizing the properties of a set of π-conjugated macrocycles has been posted on ChemRxiv.

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 []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.

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, ChemRxiv 2021, DOI: 10.26434/chemrxiv.14485002. [Preprint link, open access]