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Novel donor‐ and/or acceptor‐substituted cross‐conjugated carbocycles based on quinoids or expanded quinoids, with radiaannulene perimeters, were prepared and investigated to validate proaromaticity as a concept for reducing HOMO–LUMO gaps in push–pull chromophores. Analyses of IR, 1H NMR, and UV/Vis/NIR spectra in conjunction with molecular structures determined by X‐ray diffraction show that these...
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