Controlling the Helicity and Handedness of Polyaromatics with Isobenzofuranophane
Abstract
Abstract The extent of helicity in nonplanar polyaromatic materials affects their electronic, optical and chiroptical properties. However, controlling helicity in different systems typically requires different multistep synthetic approaches for each target compound, often with significant complexity, thereby limiting its applicability. Here, we introduce a helical synthon, isobenzofuranophane, with either a short or long tether, which enables late‐stage helicity induction and control in aromatic frameworks. We demonstrate the applicability of this synthon by reacting it with a [5]helicene aryne precursor, where both the handedness and helicene pitch are remotely‐controlled by the tether length, directly affecting the (chiro)optical properties of the helicene. The X‐ray structures support these findings with up to 35° torsion for a single benzene ring, demonstrating the potential of isobenzofuranophane to induce significant curvature to polyaromatic molecules.
Article Details
Authors (7)
Abhijeet R. Agrawal
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel
Israa Shioukhi
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel
Yinon Deree
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel
Benny Bogoslavsky
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel
Ori Shalev
The Metabolic Profiling Unit The Core Research Facility The Faculty of Medicine The Hebrew University of Jerusalem Jerusalem Israel
Roy Hoffman
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel
Ori Gidron
Institute of Chemistry and the Center for Nanoscience and Nanotechnology The Hebrew University of Jerusalem Edmond J. Safra Campus Jerusalem 9190401 Israel