Influence of helicity on the excited-state as well as chiroptical properties of two sets of regiohelical coumarins that are differentiated by "inward" and "outward" disposition of the pyran-2-one ring has been investigated. A subtle difference in the helicities manifests in divergent excited-state properties and significant differences in the dipole moments. The latter permit heretofore unprecedented regiodifferentiation in the O-H⋅⋅⋅O hydrogen-bond assisted electron-transfer quenching by phenols. Furthermore, the enantiopure hexahelical coumarins exhibit strong Cotton effects and lend themselves to a very high differentiation in the specific rotations and anisotropic dissymmetry factors. The specific rotation observed for 6-in turns out being the highest of the values reported for all hexahelicenes reported so far.
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