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The effect of the ortho alkylation of perylene bisimides on the alignment and self-assembly properties has been studied. It was found that the dichroic properties of perylene bisimides in a liquid crystal host can be reversed with a single synthetic step by ortho alkylation. Furthermore, a solvent-induced growth of ultralong organic n-type semiconducting fibrils from non- ortho-alkylated perylene bisimide was observed. Ortho substitution of the perylene bisimide core alters the mode of fibrillar growth, leading to isotropic crystallization. [ABSTRACT FROM AUTHOR]

In the molecule of the title compound, C(18)H(32)N(2)O(4), the central bicyclo-[3.3.0]octane (octa-hydro-penta-lene) has a rigid ring junction. Both rings of the bicyclo-[3.3.0]octane unit adopt an envelope conformation, and the flexible tert-butyl-carbamoyl side chains each have an extended conformation. Such a constrained bicyclo-[3.3.0]octane aliphatic template is of inter-est with respect to the design of novel self-assembling motifs. Mol-ecules related by c-glide symmetry are linked via inter-molecular N-H⋯O hydrogen bonds, forming a two-dimensional layer structure. Neighboring layers are weakly associated along the a axis due to the close approach of the tert-butyl-carbamoyl groups (2.55 Å).