Supramolecular aggregation in new crystals with nonlinear optical properties: 2-aminophenol-HClO4, 3-aminophenol-HClO4 and 4-aminophenol-HClO4

Three new hybrid crystals of 2-aminophenol-HClO4 (2-AP-HClO4, 1), 3-aminophenol-HClO4 (3-AP-HClO4, 2) and 4-aminophenol-HClO4 (4-AP-HClO4, 3) were obtained and their crystal structures determined. The 1 crystallises in centrosymmetric space group C2/c of monoclinic system while the other two (2 and 3) crystallise in the non-centro symmetric space group P21 and P212121, respectively. The oppositely charged units of the crystals, i.e. positively charged 2-APH+, 3-APH+ and 4-APH+ and ClO4−, interact via weak N+–H⋯O and O–H⋯O hydrogen bonds forming 3D-supramolecular network. Relative to KDP the SHG efficiencies are 0.62 for 2 and 0.33 for 3, measured at 1064 nm using the Kurtz–Perry method.

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