Tuning the redox profile of the 6,6′-biazulenic platform through functionalization along its molecular axis†
Shaun R.
Kelsey, 
a
Georgii
Griaznov,
a
Andrew D.
Spaeth,
a
Daron E.
Janzen,
b
Justin T.
Douglas,
c
Ward H.
Thompson
a
and
Mikhail V.
Barybin
*a
a
Georgii
Griaznov,
a
Andrew D.
Spaeth,
a
Daron E.
Janzen,
b
Justin T.
Douglas,
c
Ward H.
Thompson
a
and
Mikhail V.
Barybin
*a
Abstract
The E1/2 potential associated with reduction of the linearly-functionalized 6,6′-biazulenic scaffold is accurately correlated to the combined σp 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.
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