Enhancement of the Chiroptical Properties of o-OPE through Arene-Perfluoroarene Interactions
Year: 2025
Authors: Otero D., Martinez-Pinel A., Ortuso A.M., de Cienfuegos L.A., Cuerva J.M., Longhi G., Millbn A., Miguel D.
Autors Affiliation: Univ Granada, Dept Quim Organ, Unidad Excelencia Quim UEQ, C U Fuentenueva, Granada 18071, Spain; Univ Brescia, Dept Mol & Translat Med, I-25121 Brescia, Italy; CNR, Ist Nazl Ott INO, Res Unit Brescia, I-25123 Brescia, Italy; Univ Granada, Fac Farm, Dept Fisiol, E-18071 Granada, Spain.
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 g abs and g lum reached values of similar to 3 x 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.
Journal/Review: ORGANIC LETTERS
Volume: 27 (31) Pages from: 8459 to: 8463
More Information: This work received financial support from Grants PID2023-146801NB-C31 and PID2021-127964NB-C22 funded by MICIU/AEI/10.13039/501100011033 and ERDF, EU. A.M.O. and A.M.-P. acknowledge their FPU contracts (FPU16/02597 and FPU19/03751) funded by MCIN/AIE/10.13039/501100011033. Funding was provided also by the Italian Ministry of University and Research (MUR) (Project SMART HELIX, prot. 2022B3EFJH). Funding for open access charge: Universidad de Granada/CBUA.DOI: 10.1021/acs.orglett.5c02277
