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Perkin condensation of chrysenyl‐6‐acetic acid with chrysenylene‐6,12‐diglyoxylic acid followed by in situ esterification gives a bismaleate, whose conjugated stilbene moieties are efficiently shielded against intermolecular condensations and undergo iodine‐catalyzed oxidative photocyclization in toluene without the need for high dilution. The concentration is limited by the low solubility of the flexible bismaleate at room temperature. The so‐obtained double [7]helicene crystallizes in a nonchiral meso form. It is notably more soluble than its flexible precursor because it cannot fold to optimize π–π stacking.
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