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5,7,12,14-Tetrachloro-6,13-diaza-6,13-dihydropentacene (TCDAHP) and 5,7,12,14-tetrachloro-6,13-diazapentacene (TCDAP) were synthesized and assessed as the active channel materials for thin-film transistor applications. Analyses of the crystal structures of these molecules revealed that both exhibited slipped pi-pi stacking of the long and fused aromatic moiety. Although the packing features of the two compounds are basically identical, their highest occupied molecular orbitals, which are relevant to hole transport, are very different. Better mobility was predicted for TCDAHP over TCDAP based on the dimeric structure in the X-ray coordinates. The morphologies of thin films of TCDAHP and TCDAP prepared by thermal evaporation depend critically on the substrate on which the molecules were deposited: from the amorphous state on a SiO(2)/Si surface to the crystalline state on a pentacene buffer layer surface. The performance of thin-film transistors prepared on various substrate surfaces was studied. While no field-effect mobility was observed for these films deposited on SiO(2)/Si, a high mobility of 1.4 cm(2)/(V s) for the TCDAHP film was achieved when deposited on a pentacene buffer layer prepared on a rubbed monolayer of n-nonyltrichlorosilane on a SiO(2)/Si surface. A similar device prepared from TCDAP gave a mobility of 0.13 cm(2)/(V s).

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