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Mind the band gap: π‐conjugated pentacene di‐, tri‐, and tetramers can be synthesized by using a versatile building block in Hay homocoupling as well as Cadiot–Chodkiewicz cross‐coupling reactions. This modular approach allows the evaluation of solubility, stability, and the HOMO–LUMO gap as a function of compound length. Long‐range three‐dimensional π overlap occurs in the iBu3Si‐substituted pentacene...
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