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Molecular Patterns of Alkyl-Aryl Amides Self-assembled on a Graphite Surface

A series of amides having an alkyl chain and an aromatic head group has been prepared and their self-assembled molecular patterns on a graphite surface have been observed by scanning tunneling microscopy (STM). The molecular patterns generated appear to be defined by the relative location of the alkyl chain and aromatic ring with respect to the amide group. Thus, the molecular axis of amides derived from aromatic carboxylates and alkylamines appears to be inclined toward the lamella boundary at an angle of approximately 70°, forming mirror-image chiral domains. In contrast, the amides obtained from aromatic amines and alkyl carboxylate give a centro-symmetric molecular pattern where the molecular axis is at right angles to the lamella boundary. The relationship between the molecular ordering pattern and the structural feature of constituent molecules has been discussed.