Three dimensional molecular stacking and functionalities of aminonaphthoquinone by intermolecular hydrogen bondings and interlayer pi¯pi interactions

Three dimensional molecular stacking of aminonaphthoquinones affecting largely on their 3rd order nonlinear optical property was evaluated by X-ray crystal analysis. It was found that the intermolecular hydrogen bondings and the interlayer pi¯pi interactions played a significant role in producing large bathochromic shifts of absorption maximum in solid state, and gave large 3rd order nonlinear optical susceptibility. Molecular symmetry and substituent effects on their physical properties were also correlated with their molecular stacking in crystals.