A twin-tapered bi-1,3,4-oxadiazole derivative (BOXD-T8) showed a monomeric feature and intramolecular charge transition at concentrations lower than 10(-5) mol/L. BOXD-T8 molecules self-assembled to nanoparticles and further to helical nanofibers with blue fluorescence emission in DMSO, while nanoribbons resulted in an emission-enhanced gel in ethanol. The strong fluorescent emissions of BOXD-T8 in an isolated state in apolar solvents were attributed to the coplanar conformation of the rigid backbone and the strong fluorescent emissions of BOXD-T8 in the aggregation states were attributed to the coplanar conformation of the rigid backbone and J aggregation.