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We report two families of naphthalenediimides (NDIs) symmetrically functionalized with discrete carbon chains comprising up to 55 carbon atoms ( C    n    -NDI-C    n   , n = 39, 44, 50, and 55) and their self-assembly at the 1-phenyloctane/highly oriented pyrolytic graphite interface (1-PO/HOPG interface). The compounds differ by the presence or absence of two or three internal double bonds in the carbon chains (unsaturated and saturated C    n    -NDI-C    n   , respectively). Combinatorial distributions of geometrical isomers displaying either the E - or Z -configuration at each double bond are obtained for the unsaturated compounds. Analysis of the self-assembled monolayers of equally long unsaturated and saturated C    n    -NDI-C    n   by scanning tunneling microscopy (STM) reveal that all C    n    -NDI-C    n   tend to form lamellar systems featuring alternating areas of aromatic cores and carbon chains. Extended chain lengths are found to significantly increase disorder in the self-assembled monolayers due to misalignments and enhanced strength of interchain interactions. This phenomenon is antagonized by the local order-inducing effect of the internal double bonds: unsaturated C    n    -NDI-C    n   give qualitatively more ordered self-assembled monolayers compared to their saturated counterparts. The use of combinatorial distributions of unsaturated C    n    -NDI-C    n   geometrical isomers does not represent a limitation to achieve local order in the self-assembled monolayers. The self-assembly process operates a combinatorial search and selects the geometrical isomer(s) affording the most thermodynamically stable pattern, highlighting the adaptive character of the system. Finally, the antagonistic interplay between the extended carbon chain lengths and the presence of internal double bonds brings to the discovery of the lamellar "phase C" morphology for unsaturated C    n    -NDI-C    n   with n ≥ 50.

Combinatorial Selection Among Geometrical Isomers of Discrete Long-Carbon-Chain Naphthalenediimides Induces Local Order at the Liquid/Solid Interface