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The natural phylloxanthobilin Z 1 and its methyl ester Z 1‐Me behave as medium‐responsive photoswitches. In polar solvents, the Z and E isomers photointerconvert reversibly, but in apolar solvents or in membrane‐mimetic micellar solutions, Z 1 and Z 1‐Me preorganize by hydrogen‐bonded self‐assembly and undergo [2+2] photocycloadditions to the C 2‐symmetric octapyrroles 2 and 2‐Me, respectively.
