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Issue 11, 2014
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Conjugated oligomers incorporating azulene building blocks – seven- vs. five-membered ring connectivity

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Abstract

The properties of isomeric azulene derivatives based on 7- versus 5-membered ring substitution were examined by the synthesis and characterization of well-defined electroactive oligomers. The substitution pattern was shown to dramatically influence solid-state, electronic and optical properties of the oligomers with acid-responsive materials only being observed when the azulenium cation could be directly stabilized by substituents in the 7-membered ring. Protonation was accompanied by a reversible color change and a strong red-shift of the absorption maximum as indicated by UV-vis studies. In addition, we show that the absorption maxima and optical band-gaps of azulenium cations can be tuned by the nature of the chromophore connected to the seven-membered ring of the azulene nucleus.

Graphical abstract: Conjugated oligomers incorporating azulene building blocks – seven- vs. five-membered ring connectivity

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Submitted
24 Jul 2014
Accepted
27 Jul 2014
First published
07 Aug 2014

Chem. Sci., 2014,5, 4483-4489
Article type
Edge Article
Author version available

Conjugated oligomers incorporating azulene building blocks – seven- vs. five-membered ring connectivity

E. Amir, M. Murai, R. J. Amir, J. S. Cowart, M. L. Chabinyc and C. J. Hawker, Chem. Sci., 2014, 5, 4483
DOI: 10.1039/C4SC02210F

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