biostudies-literatureKelsey SRNational Science Foundation Graduate Research Fellowship ProgramNCRR NIH HHSNIH Office of the DirectorNational Science Foundation5213-5216https://www.ebi.ac.uk/biostudies/studies/S-EPMC11080966biostudies-literatureUnknown60(39)The <i>E</i>_1/2 potential associated with reduction of the linearly-functionalized 6,6'-biazulenic scaffold is accurately correlated to the combined <i>σ</i>_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.Chemical communications (Cambridge, England)Tuning the redox profile of the 6,6'-biazulenic platform through functionalization along its molecular axis.PMC11080966P20 GM103418MRI-2117449S10 RR024664CHE-9977422DGE-1940699CHE-1808120MRI-1125975CHE-1625923S10OD016360S10RR024664Kelsey SRBarybin MVGriaznov GSpaeth ADDouglas JTJanzen DEThompson WHfalseTuning the redox profile of the 6,6'-biazulenic platform through functionalization along its molecular axis.The <i>E</i>_1/2 potential associated with reduction of the linearly-functionalized 6,6'-biazulenic scaffold is accurately correlated to the combined <i>σ</i>_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.2024-01-01T00:00:00Z2024 May2026-05-29T09:37:11.427Z2026-05-19T03:07:15.453ZS-EPMC110809663865207310.1039/d4cc00656a