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. 2025 Aug 8;27(31):8459-8463.
doi: 10.1021/acs.orglett.5c02277. Epub 2025 Jul 30.

Enhancement of the Chiroptical Properties of o-OPE through Arene-Perfluoroarene Interactions

Darío Otero  1 , Álvaro Martínez-Pinel  1 , Ana M Ortuño  1 , Luis Álvarez de Cienfuegos  1 , Juan M Cuerva  1 , Giovanna Longhi  2   3 , Alba Millán  1 , Delia Miguel  4
Affiliations

Enhancement of the Chiroptical Properties of o-OPE through Arene-Perfluoroarene Interactions

Darío Otero et al. Org Lett. .

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.

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Figures

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1
Working hypothesis and structure of enantiopure (S,S,P)-1-F n .
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1. Synthesis of (S,S,P)-1-F n
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Structures (left) of (S,S,P)-1-F 1 (top), (S,S,P)-1-F 3 (middle), and (S,S,P)-1-F 5 (bottom). UV–vis (solid line) and fluorescence (dashed line) spectra (center) of (S,S,P)-1-F n . ECD (solid line) and CPL (dashed line) (right) of (S,S,P)-1-F n (red line) and (R,R,M)-1-F n (black line). All of the spectra were recorded using 1.5 × 10–5 M solutions in CH2Cl2.
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