Pentahelicene (PH) exhibits the largest absorption (g(abs)) and luminescence (g(lum)) dissymmetry factors among the helicene family but is configurationally and (photo)chemically labile, encumbering its application to chiroptical materials. To bypass the pitfalls, three PH units are merged in a single molecule to build D-3-symmetric triple pentahelicene, hexabenzotriphenylene (HBT), which attains indeed the configurational and (photo) chemical robustness through equilibrium with a C-2-symmetric conformer that interrupts the racemization and photocyclization. UV-vis, circular dichroism (CD), and circularly polarized luminescence (CPL) spectral examinations reveal the significantly larger g(abs) and g(lum) values for HBT than for any of configurationally robust single [n]helicene (n >= 6) and C-2-symmetric triple pentahelicene, trinaphthotriphenylene (TNT). Theoretical calculations precisely reproduce the main features of the experimental CD and CPL spectra of PH, HBT, and TNT, and the relevant electric and magnetic transition moments and their mutual angles well rationalize the relative CD and CPL intensities of all the single and triple pentahelicenes.