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The application of the principle of kinetic stabilization on vinylogous 6-(cyclopentadienyl)pentafulvenes 1 led to the synthesis of the di- and tetra-tert-butyl derivatives 7a – e and 8a - c. Their reactions with bases and acids form charged, heteroatom-free cyanine-type carbanionic 9a - e, 10a – e and carbocationic 11a – e, 12a – c species which were characterized with NMR and UV/Vis spectroscopy. Conclusions on the ion pair structures of the alkali metal salts 9a - e and 10a – c are drawn from the spectroscopic data. Additionally, in one case the behavior of the alkali metal salt 10b towards oxidants was studied by cyclic voltammetry and the structure of the corresponding hydrocarbon 8b was proved by X-ray structural analysis.