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A series of semiconducting and symmetrical 2,9-dialkylpentacenes was successfully synthesized via a five-step process and their structures confirmed by 1 H NMR, IR and elemental analyses. Their liquid crystallinity was investigated by differential scanning calorimetry and polarizing optical microscopy. The introduction of alkyl chains also improved their solubility. For alkyl chains longer than butyl, focal conic or baton texture was observed, indicating the existence of an ordered smectic phase. Thermal analyses revealed that the both melting and smectic-isotropic transition temperatures show an odd-even effect when the alkyl chain is larger than heptyl or octyl. The synthesized compounds are promising candidates for semiconductors in organic field-effect transistors because their liquid crystallinity allows easy molecular alignment in the device fabrication process.

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