A novel amphiphile 2,4-dihydroxy-N-octadecylbenzylideneamine (abbreviated as SBC 1 8 ) bearing a schiff base moiety as headgroup, and its complex Bis(2,4-dihydroxy-N-octadecylbenzylideneaminato) Copper(II) (abbreviated as Cu(SBC 1 8 ) 2 ) were synthesized successfully. The π-A isotherms were conducted to explore their monolayer behavior. The π-A isotherm of an SBC 1 8 monolayer shows that an orientational change may be accompanied by increase of intramolecular hydrogen bonds in the plateau-like region, which were further confirmed by FTIR and UV-Vis spectroscopic results. By Comparison the plateau-like region disappeared in π-A isotherms of surface film and subphase film of Cu (SBC 1 8 ) 2 which may be due to coordination of Cu 2 + to SBC 1 8 eliminating conversion of intermolecular to intramolecular hydrogen bonds.