In order to investigate the supramolecular assembly and intermolecular hydrogen bonding of special amphiphile, a trigonal Schiff base compound was designed and synthesized, and it supramolecular assembly and interaction properties were investigated by spectral measurements. It was found that the Schiff base compound can be spread on water surface to form stable monolayer. When it was spread on the subphase containing barbituric acid, it can show hydrogen bonding interaction with barbituric acid. Due to the directionality and strong matching of hydrogen bond, two barbituric acid molecules can be encapsulated into intramolecular space of the trigonal Schiff base compound through intermolecular H-bonding to form a 1:2 complex. A rational complex mode was proposed.