Dumbbell-shaped aromatic amphiphilic molecules consisting of a dodeca-p-phenylene as a rigid segment and oligoether dendrons as a flexible chains were synthesized, characterized, and their aggregation behavior was investigated in the bulk and at the air-water interface. In contrast to the molecule 2 which shows a nematic liquid crystalline state, molecule 1 based on shorter dendritic chains was observed to self-assemble into a 3-D primitive orthorhombic supercrystal. And molecule 1 at the air-water interface was observed to reorganize from circular plates to ring structures by lateral compressions.