Helicenes are chiral organic dyes that are attracting growing attention due to the high tunability of their (chir)optical and electronic properties. In this work, a series of functionalized cationic diaza[4]helicenes based on dimethoxyquinacridinium (DMQA) scaffolds are presented. By merging branched N-alkyl side chains and triple para-functionalization with OMe groups, structures combine improved chiroptical responses (5x increase) and strong fluorescence quantum yields (φf ≈ 70% in acetonitrile). An overall improved efficiency of the emission of circularly polarized light with BCPL values reaching 3.4 M^-1 cm^-1 is obtained. Additionally, two-photon excitation (2PE) studies were performed, showing good values of cross section at 810 nm. Interestingly, 2PE CPL spectra were acquired for the most performant derivatives (N-isopropyl and N-cyclohexyl); this type of measurement being usually challenging for organic molecular species. Finally, the viability of these compounds in single and two-photon excitation microscopy is also shown.