Enhancement of the Chiroptical Properties of o‑OPE through Arene−Perfluoroarene Interactions

Abstract

In this work, we synthesized and studied fluorinated o-oligophenylene ethynylenes (o-OPEs). Arene−perfluoroarene interactions promote the folding of the extremes of the OPE stabilizing folded conformations and extending the helical conformation to two complete turns, thus improving their chiroptical responses compared to the nonfluorinated analogue. Dissymmetry factors gabs and glum reached values of ∼3 × 10−2 on the perfluorinated compound, which represents a 3-fold increase compared to that of the nonfluorinated analogue and is an exceptional value for a small organic molecule.