Conjugated oligoelectrolytes (COEs) are amphiphilic, fluorogenic molecules that spontaneously associate with\u00a0lipid bilayer membranes\u00a0and are gaining attention as molecular reporters, particularly for exosome detection by flow\u00a0cytometry. Questions nonetheless remain on how to best design COEs for optimal performance and on the geometry of lipid bilayer intercalation. In response, we designed a series of oligo-phenylenevinylene COEs with varying lengths and numbers of charged groups to address these uncertainties. Examination of the organization within lipid bilayers through\u00a0polarized fluorescence\u00a0microscopy shows that the\u00a0optical transition\u00a0moments are perpendicular to the bilayer plane, with the conjugated segment flanked by\u00a0hydrophobic\u00a0phospholipid\u00a0tails. COEs initially form a disorganized layer on the vesicle periphery, reflecting\u00a0electrostatic\u00a0association before intercalation. Uptake experiments show that longer dimensions and increased numbers of charges allow for a higher degree of cellular association. Both shorter core length and increased number of charges accelerate the rate needed to achieve emission saturation.<\/p>\n