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Azulenoisoindigo: A Building Block for π-Functional Materials with Reversible Redox Behavior and Proton Responsiveness
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Azulene, one of representative nonbenzenoid aromatic hydrocarbons,
exhibits unique molecular structure and distinctive physical and chemical
properties. Herein, an azulene-based isoindigo analogue, azulenoisoindigo (
AzII
)
is designed and synthesized, which has a twisted molecular backbone and
R/S-isomers in single crystals. Interestingly,
AzII
shows the characteristics of both isoindigo and azulene, such
as completely reversible redox behavior and reversible proton responsiveness.
UV-vis-NIR,
1
H NMR and electron paramagnetic resonance (EPR)
measurements were carried out to get insights into the possible mechanism of
the proton-responsive property of
AzII
.
The results demonstrated that only one azulenyl moiety of molecule of
AzII
was protonated and deprotonated,
and the protonated
AzII
can be
further oxidized to form azulenium cation radicals.
American Chemical Society (ACS)
Title: Azulenoisoindigo: A Building Block for π-Functional Materials with Reversible Redox Behavior and Proton Responsiveness
Description:
Azulene, one of representative nonbenzenoid aromatic hydrocarbons,
exhibits unique molecular structure and distinctive physical and chemical
properties.
Herein, an azulene-based isoindigo analogue, azulenoisoindigo (
AzII
)
is designed and synthesized, which has a twisted molecular backbone and
R/S-isomers in single crystals.
Interestingly,
AzII
shows the characteristics of both isoindigo and azulene, such
as completely reversible redox behavior and reversible proton responsiveness.
UV-vis-NIR,
1
H NMR and electron paramagnetic resonance (EPR)
measurements were carried out to get insights into the possible mechanism of
the proton-responsive property of
AzII
.
The results demonstrated that only one azulenyl moiety of molecule of
AzII
was protonated and deprotonated,
and the protonated
AzII
can be
further oxidized to form azulenium cation radicals.
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