Stimuli-Responsive Azulene-Based Conjugated Oligomers with Polyaniline-like Properties

Amir, E.; Amir, R.J.; Campos, L.M.; Hawker, C.J. J. Am. Chem. Soc.
J. Am. Chem. Soc.
133, 10046-10049.

Novel azulene building blocks, prepared via the cycloaddition of thiophene-S,S-dioxides and fulvenes, allow for incorporation of the seven-membered ring of the azulene nucleus directly into the backbone of conjugated materials. This unique mode of incorporation gives remarkably stable, stimuli-responsive materials upon exposure to acid. This simple doping/dedoping strategy provides for effective optical band gap control and on/off fluorescence switching, reminiscent of polyaniline.