Tuning the redox profile of the 6,6'-biazulenic platform through functionalization along its molecular axis

Shaun R Kelsey; Georgii Griaznov; Andrew D Spaeth; Daron E Janzen; Justin T Douglas; Ward H Thompson; Mikhail V Barybin

doi:10.1039/d4cc00656a

Tuning the redox profile of the 6,6'-biazulenic platform through functionalization along its molecular axis

Chem Commun (Camb). 2024 Apr 23. doi: 10.1039/d4cc00656a. Online ahead of print.

Authors

Shaun R Kelsey¹, Georgii Griaznov¹, Andrew D Spaeth¹, Daron E Janzen², Justin T Douglas³, Ward H Thompson¹, Mikhail V Barybin¹

Affiliations

¹ Department of Chemistry, University of Kansas, Lawrence, KS 66045, USA. mbarybin@ku.edu.
² Department of Chemistry and Biochemistry, St. Catherine University, St. Paul, MN 55105, USA.
³ NMR Laboratory, Molecular Structures Group, University of Kansas, Lawrence, KS 66047, USA.

PMID: 38652073
DOI: 10.1039/d4cc00656a

Abstract

The E_1/2 potential associated with reduction of the linearly-functionalized 6,6'-biazulenic scaffold is accurately correlated to the combined σ_p Hammett parameters of the substituents over >600 mV range. X-ray crystallographic analysis of the 2,2'-dichloro-substituted derivative revealed unexpectedly short C-Cl bond distances, along with other metric changes, suggesting a non-trivial cycloheptafulvalene-like structural contribution.