McGill Seminar: Michael Haley- The Interplay Between Antiaromaticity and Diradical Character in Diarenoindacenes and Diindenoarenes

Abstract:

This talk will present our synthetic, structural, computational and materials studies of a class of carbon-rich semiconducting molecules based on the indenofluorene (IF) skeleton.¹ Access to the fully conjugated, 20 π-electron, formally antiaromatic system is accomplished via a variety of intermediate diones. These molecules in turn can be assembled via well-known organic possesses (Suzuki cross-coupling, benzylic oxidation, Friedel-Crafts acylation/alkylation).¹ Optimization of their synthesis now permits access to IF derivatives in multigram quantities. We have shown that thin films or single crystals of several different IF scaffolds can serve as an active layer in organic field effect transistors (OFETs).² 

1. (a) Frederickson, Rose & Haley, Acc. Chem. Res. 2017, 50, 977; (b) Dressler & Haley, J. Phys. Org. Chem. 2020, 33, e4114.

2. (a) Marshall et al., Chem. Sci. 2016, 7, 5547; (b) Zeidell et al., Chem. Mater. 2019, 31, 6962.

3. (a) Frederickson, Zakharov & Haley, J. Am. Chem. Soc. 2016, 138, 16827; (b) Frederickson et al., Synlett 2018, 29, 2562.

4. (a) Rudebusch et al., Nat. Chem. 2016, 8, 753; (b) Dressler et al., Nat. Chem. 2018, 10, 1134; (c) Barker et al., J. Am. Chem. Soc. 2020, 142, 1548; (d) Dressler et al., Chem 2020, 6, 1353; (e) Hayashi, Barker et al., J. Am. Chem. Soc. 2020, 142, 20444.

Bio:

Michael M. Haley received both B.Sc. (1987) and Ph.D. (1991) degrees from Rice University working with Ed Billups on the chemistry of cyclopropenes and cycloproparenes. He then pursued his postdoctoral studies with Peter Vollhardt at UC-Berkeley studying [N]phenylenes and joined the faculty at the U Oregon in 1993 where he is currently the Richard and Patricia Noyes Professor of Chemistry. He also served as Head of the Department from 2008 to 2014. He is a well-recognized expert in the synthesis and study of aromatic and carbon-rich molecules with applications in materials science. He has co-authored over 230 papers published in some of the most respected chemistry journals (Nature Chem., JACS, Angew. Chem., Chem, etc.). Haley’s research was recognized with the 2021 ACS George Olah Award in Hydrocarbon or Petroleum Chemistry. Other recent awards include Humboldt Research Fellowship (2015), JSPS Research Fellowship in Japan (2016), election to “Senior Member” of the US National Academy of Inventors (2019), and “Mercator” Fellowship at the Justus-Liebig-University of Gießen (2021-2025). Haley served on the joint Editorial Advisory Board for the journals Synthesis, Synlett and J. Phys. Org. Chem.