Aromatic molecules are inherently rigid among organic systems. The rigidity of aromatic systems leads to strong luminescent properties, -stacking abilities, efficient carrier transport, and so on. On the other hand, conformational flexibility is useful for switching molecular properties. To combine the advantages of rigidity and flexibility, we have designed and synthesized flapping molecules (FLAP) that consists of rigid aromatic wings and a flexible COT (cyclooctatetraene) joint. In this article we introduce unique photofunctional materials based on the rigid-flexible hybrid molecular systems.