Bolaforms B-1, B-2, and B-3 of the formulas, Br-Me3N+(CH2)(10)N+Me3Br-, Br-Me3N+(CH2)(10)OH, and Br-Me3N+(CH2)(10)COO-Na+, respectively, were synthesized, and their properties in the bulk as well as at the air/aqueous NaBr (10 mM) solution interface have been studied. Their interactions with sodium dodecyl sulfate (SDS) and cetyltrimethylammonium bromide (CTAB) also have been investigated. Tensiometry, conductometry, spectrophotometry, and microcalorimetry techniques were used for characterization and estimation. Both pure bolaforms and their mixtures with SDS and CTAB have been found to self-aggregate, forming micelles in solution. The mixed systems of bolaform and SDS have been observed to form both micelles and vesicles. Their mutual interactions were synergistic, which at the interface was more spontaneous than in the bulk. The interfacial and bulk compositions of the mixed binary systems (bolaform and SDS or CTAB) with their associated interaction parameters have been estimated from the Rosen interaction model and the regular solution theory of Rubingh, respectively. The formed vesicles have been found to entrap the water-soluble dye, bromophenol blue, and the dye solubilized vesicles of B-1-SDS and B-2-SDS completely eluted out of the sephadex column proving their formation. A rough estimation of the size and polydispersity index of the formed micelles and vesicles has been made from DLS measurements.