Interesting ChemistryChemical Sciences

Molecules of the year – 2019: twisty tetracene.

https://doi.org/10.59350/3g9fe-y7702
Published in Henry Rzepa's Blog

All of the molecules in this year’s C&EN list are fascinating in their very different ways. Here I take a look at the twisty tetracene (dodecaphenyltetracene) which is indeed very very twisty.[cite]10.1002/anie.201812418[/cite] Click on image to view 3D model Unfortunately, the authors point that the twisty-ness does not lead to a stable helical configuration at room temperatures and so separate enantiomers cannot be isolated.

References

General ChemistryCatalysis

Dodecaphenyltetracene

https://doi.org/10.1002/anie.201812418
Published in Angewandte Chemie International Edition
Authors Yonglong Xiao, Joel T. Mague, Russell H. Schmehl, Farihah M. Haque, Robert A. Pascal

AbstractDodecaphenyltetracene (4), the largest perphenylacene yet prepared, was synthesized from known tetraphenylfuran, hexaphenylisobenzofuran, and 1,2,4,5‐tetrabromo‐3,6‐diphenylbenzene in three steps. The X‐ray structure of the deep red, highly luminescent 4 shows it to be a D2‐symmetric molecule with an end‐to‐end twist of 97°. The central acene is encapsulated by the peripheral phenyl substituents, and as a result, the molecule is relatively unreactive and even displays reversible electrochemical oxidation and reduction.