A novel bolaamphiphile surfactant N,N0-(octane-1,8-diyl)bis(pyrrolidine-2-carboxamide)(DAOP), was designed and synthesized from proline and 1,8-diaminooctane, as the hydrophilic part and hydrophobic part, respectively. After separation and purification, the structures of the synthesized bola surfactants were verified by IR, MS and~1 H NMR. The p Kawas measured by a titration experiment, the turbidity was determined using a Shimadzu UV-1750 spectrophotometer, and the critical micelle concentration(CMC)values of the synthesized surfactants in water were obtained using the conductivity and fluorescence probe measurements. The synthesized bolaamphiphile surfactants demonstrate the ability of selfassemble to form vesicles that were confirmed with dynamic light scattering and transmission electron microscopy. The results showed that the novel bolaamphiphile surfactant derived from proline might potentially be an excellent carrier for drug delivery. A novel bolaamphiphile surfactant N, N- octane-1,8-diyl bis (pyrrolidine-2-carboxamide) (DAOP) was designed and synthesized from proline and 1,8-diaminooctane, as the hydrophilic part and hydrophobic part, respectively. After separation and purification, the structures of the synthesized bola surfactants were verified by IR, MS and ~ 1 H NMR. The p Kawas measured by a titration experiment, the turbidity was determined using a Shimadzu UV-1750 spectrophotometer, and the critical The synthesized bolaamphiphile surfactants demonstrates the ability of selfassemble to form vesicles that were confirmed with dynamic light scattering and transmission electron microscopy. The results said that the novel bolaamphiphile surfactant derived from proline might potentially be an excellent carrier for drug delivery.