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Trans Z‐type ( Trans ‐1 ) and cis‐∏‐type ( Cis‐Rac ‐1 ) dimers were designed and prepared via intermolecular [2+2] photocycloaddition. Cis‐Rac ‐1 adopts a distinctive bisplanar geometry, giving rise to an unprecedented type of planar chirality. The resulting planar‐chiral compounds exhibit good solubility and chiral stability. These findings establish a general and straightforward strategy for constructing planar chirality, opening new avenues for the design of planar‐chiral functional materials. More details are discussed in the article by Tang et al . on pages 2481—2486. image