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The guanine nucleobase aggregates into tetrameric or different ribbon structures on surfaces or in solution. The preference of guanine for a particular ribbon structure over other arrangements under experimental settings is explained quantum chemically. An important cooperative effect of the σ electronic system in the hydrogen bonding is revealed for the switching between different self‐assembled structures. More information can be found in the Full Paper by C. Fonseca Guerra and G. Paragi on page 3042 ff. [ABSTRACT FROM AUTHOR]