N,N′-Dicyclo­hexyl­naphthalene-1,8;4:5-dicarboximide

The title compound, C26H26N2O4, synthesized by the reaction of naphthalene-1,4,5,8-tetra­carboxylic acid anhydride and cyclo­hexyl­amine, exhibits good n-type semiconducting properties. Accordingly, thin-film transistor devices comprising this compound show n-type behavior with high field-effect electron moblity ca 6 cm2/Vs [Shukla, Nelson, Freeman, Rajeswaran, Ahearn, Meyer & Carey(2008 ▶). Chem. Mater. Submitted]. The asymmetric unit comprises one-quarter of the centrosymmetric mol­ecule in which all but two methyl­ene C atoms of the cyclo­hexane ring lie on a mirror plane; the point-group symmetry is 2/m. The naphthalene­diimide unit is strictly planar, and the cyclo­hexane rings adopt chair conformations with the diimide unit in an equatorial position on each ring

N,N′-Bis(2,2,3,3,4,4,4-hepta­fluoro­butyl)naphthalene-1,4:5,8-tetra­carboximide

The title mol­ecule, C22H8F14N2O4, lies across a crystallographic inversion center with the naphthalene diimide core essentially planar (mean deviation from plane is 0.0583 Å). The CF2 groups in the perfluorobutyl chains are in an energetically favorable all trans conformation. In the crystal structure, mol­ecules are packed in slightly displaced layers so that the side chains overlap the aromatic naphthalene diimide rings, thus minimizing any possible π–π overlap