Crystal structure of N,N ′-bis(cyclohexyl)-1-(N,N-dihexylamino)perylene-3,4:9,10-bis(dicarboximide)

Abstract

ABSTRACTAn asymmetric dialkylamino-substituted perylene bisimide (1), N,N′-bis(cyclohexyl)-1-(N,N-dihexylamino)perylene-3,4:9,10-bis(dicarboximide), was synthesized and characterized by single-crystal X-ray diffraction. The crystal belongs to triclinic, space group P–1, with a = 9.8924(6), b = 14.6338(10), c = 15.6221(10) Å, α= 105.098(3)°, β = 103.386(2)°, γ = 107.772(3)°, and Z = 2. The central perylene core of 1 is twisted with dihedral angles of 14.9(3)° and 11.6(3)°; this twist configuration induces the axial chirality in this family of perylene bisimide dyes. In the crystal structure, the intermolecular C–H···O interaction links a pair of molecules into a cyclic centrosymmetric dimer that is connected to one another via the intermolecular π–π stacking, so linking the molecules into a continuous one-dimensional framework along the [100] direction.