Enhancement of the Chiroptical Properties of <i>o</i>-OPE through Arene–Perfluoroarene Interactions
In this work, we synthesized and studied fluorinated <i>o</i>-oligophenylene ethynylenes (<i>o</i>-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 <i>g</i><sub>abs</sub> and <i>g</i><sub>lum</sub> reached values of ∼3 × 10<sup>-2</sup> 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.
Authors
- Juan M. Cuerva (ORCID: https://orcid.org/0000-0001-6896-9617)
- Álvaro Martínez-Pinel (ORCID: https://orcid.org/0000-0001-6037-5347)
- Giovanna Longhi (ORCID: https://orcid.org/0000-0002-0011-5946)
- Ana M. Ortuño
- D. Miguel (ORCID: https://orcid.org/0000-0002-7876-3986)
- Alba Millán (ORCID: https://orcid.org/0000-0003-2754-270X)
- Luı́s Álvarez de Cienfuegos (ORCID: https://orcid.org/0000-0001-8910-4241)
- Darío Otero
Institutions
- Universidad de Granada (ES)
- National Institute of Optics (IT)
- Instituto de Química y Fisicoquímica Biológicas (AR)
- Instituto de Química Orgánica General (ES)
- University of Brescia (IT)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-30
- DOI
- https://doi.org/10.1021/acs.orglett.5c02277
- Citations
- 4
- Primary Topic
- Synthesis and Properties of Aromatic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- Ministerio de Ciencia, Innovación y Universidades
- Universidad de Granada
- Ministero dell'Università e della Ricerca
- European Regional Development Fund
- Agencia Estatal de Investigación