Electron Delocalization in Perylene Diimide Helicenes

Nathaniel J Schuster; Daniel W Paley; Steffen Jockusch; Fay Ng; Michael L Steigerwald; Colin Nuckolls

doi:10.1002/anie.201607878

Electron Delocalization in Perylene Diimide Helicenes

Angew Chem Int Ed Engl. 2016 Oct 17;55(43):13519-13523. doi: 10.1002/anie.201607878. Epub 2016 Sep 26.

Authors

Nathaniel J Schuster¹, Daniel W Paley¹, Steffen Jockusch¹, Fay Ng¹, Michael L Steigerwald², Colin Nuckolls³

Affiliations

¹ Chemistry Department, Columbia University, New York, NY, 10027, USA.
² Chemistry Department, Columbia University, New York, NY, 10027, USA. mls2064@columbia.edu.
³ Chemistry Department, Columbia University, New York, NY, 10027, USA. cn37@columbia.edu.

PMID: 27717214
DOI: 10.1002/anie.201607878

Abstract

We report two new helicenes derived from the double fusion of an acene with two perylene diimide (PDI) subunits. These PDI-helicene homologs exhibit very different structural and electronic properties, despite differing by only a single ring in the link between the PDI units. The shorter inter-PDI link brings the two PDI subunits closer together, and this results in the collision of their respective π-electron clouds. This collision facilitates intramolecular through-space electronic delocalization when the PDI-helicene is reduced.

Keywords: chirality; helicenes; mixed-valence compounds; perylene diimide; π-π interactions.

Publication types

Research Support, U.S. Gov't, Non-P.H.S.
Research Support, Non-U.S. Gov't