A novel pH-responsive and photo-isomerizing β-cyclodextrin (β-CD) derivative DACD was synthesized and fully characterized by 1 H-NMR, 13 C-NMR, and HRMS. At room temperature, this compound would self-assemble to layer aggregations in an aqueous environment. The aggregated state can reversibly switch to a monomeric solution state attributed to the hydrophobic competition of an additional substance to the β-CD cavity. This self-aggregatable cyclodextrin derivative based nanosystem functioned by switching between the aggregated and monomeric state. An effective address-crossing digital information system, in response to pH and UV stimuli, was demonstrated based on such mechanism. This chemical system, capable of data memories and logic functions in nanoscale, can mimic the functions of pointer-based data processing.