The recently synthesized triaroylbenzene unit represents a novel and versatile core structure for the creation of derivatives exhibiting supramolecular organization at interfaces. Monolayers of triaroylbenzene derivatives bearing three octyl groups projecting away from the molecular core and terminated by hydroxyl, carboxylic acid, and methyl ester groups have been studied using surface pressure versus molecular area isotherm measurements and observations by Brewster angle microscopy (BAM). The octyl derivative appears to form a monolayer of limited stability. The remaining derivatives form monolayers for which the surface pressure begins rising at very high molecular areas of 350-500 square angstroms per molecule. The derivatives with hydrophilic end-groups on the octyl chains exhibit collapse areas near 40-50 square angstroms per molecule and collapse pressures such that a reorientation at the water surface under compression from a sort of 'face-on' to 'edge-on' arrangement appears likely as an explanation for the data. At intermediate molecular areas, a phase transition occurs and aggregate formation becomes clearly visible under BAM. Studies of the methyl ester derivative mixed with methyl stearate using BAM exhibit a contrast inversion between a background phase and immiscible domains of methyl stearate during compression that lends support to the concept of a conformational reorientation of the triaroylbenzene derivatives during compression.