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A representati e -conjugated motif, perylenediimide (PDI), when functionalized with taper-shaped semi-fluoroalkyl chains at one of its imide positions, self-assembled into various ordered phase structures depending on the type of side chains at the other imide position. Asymmetrical substitution by semi-fluoroalkyl/alkyl chains allowed the PDI molecule to form a rectangular columnar liquid crystalline mesophase while semi-fluoroalkyl/ triethyleneglycol-substitution resulted in a lamellar-packed crystalline mesophase. In both mesophases, the immiscible nature of superhydrophobic/hydrophobic or superhydrophobic/hydrophilic segments works as the major droving force to lead semi-fluoroalkyl/alkyl or semi-fluoroalkyl/oxyethyleneglycol nano-domains, resulting in high stability of the mesophases with the wide temperature range over 100oC. The compound decorated with tapered semi-fluoroalkyl chains at the both imide positions exhibited complicated crystalline ordered phases with high thermal stability.

Side Chain-Directed Assembly of Large Discotic π-Conjugated Molecules: Toward Tuning and Stabilization of Mesophases