Adaptive Cinchona Alkaloid-Derived Organoboron Crystalline Sponges Enable Enantioseparation of Weakly Interacting Molecules.
- 1Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664Warsaw, Poland.
- 2Institute of Physical Chemistry, Polish Academy of Sciences , Kasprzaka 44/52, 01-224Warsaw, Poland.
Abstract
The enantioseparation of small, weakly interacting organic molecules remains a fundamental challenge, as they lack the functional groups required for efficient chiral recognition. Consequently, their enantiopure forms are typically accessed via asymmetric synthesis rather than resolution. Herein, we demonstrate that adaptive supramolecular crystalline sponges assembled from air- and moisture-stable cinchona alkaloid-derived organoboron complexes enable efficient enantiodiscrimination of small ethers, lactones, and cyclic ketones through guest inclusion within porous crystalline frameworks. Structural analysis reveals that enantioselectivity arises from adaptive confinement within homochiral cavities, where subtle framework rearrangements and modulation of cavity volume amplify cooperative weak host-guest interactions. Systematic tuning of the molecular building blocks affords crystalline sponges capable of resolving challenging substrates such as the biobased green solvent 2-methyltetrahydrofuran, γ-valerolactone, and methylcyclohexanone isomers with enantiomeric excesses of up to 76%. These findings establish adaptive confinement in supramolecular crystalline sponges as a general mechanism for chiral discrimination in the solid state and provide a conceptual framework for enantioseparation beyond conventional crystallization-based approaches.
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BibTeX
@article{rajski2026adaptive,
title = {{Adaptive Cinchona Alkaloid-Derived Organoboron Crystalline Sponges Enable Enantioseparation of Weakly Interacting Molecules.}},
author = {Maximilian Rajski and Michał Terlecki and Iwona Justyniak and Arkadiusz Kornowicz and Michał K Leszczyński and Mikołaj Cieślak and Janusz Lewiński},
journal = {Journal of the American Chemical Society},
year = {2026},
month = oct,
doi = {10.1021/jacs.6c09766},
url = {https://europepmc.org/article/MED/42954513},
note = {CC BY},
}
RIS
TY - JOUR
TI - Adaptive Cinchona Alkaloid-Derived Organoboron Crystalline Sponges Enable Enantioseparation of Weakly Interacting Molecules.
AU - Maximilian Rajski
AU - Michał Terlecki
AU - Iwona Justyniak
AU - Arkadiusz Kornowicz
AU - Michał K Leszczyński
AU - Mikołaj Cieślak
AU - Janusz Lewiński
PY - 2026
DA - 2026/10/01
JO - Journal of the American Chemical Society
DO - 10.1021/jacs.6c09766
UR - https://europepmc.org/article/MED/42954513
AB - The enantioseparation of small, weakly interacting organic molecules remains a fundamental challenge, as they lack the functional groups required for efficient chiral recognition. Consequently, their enantiopure forms are typically accessed via asymmetric synthesis rather than resolution. Herein, we demonstrate that adaptive supramolecular crystalline sponges assembled from air- and moisture-stable cinchona alkaloid-derived organoboron complexes enable efficient enantiodiscrimination of small ethers, lactones, and cyclic ketones through guest inclusion within porous crystalline frameworks. Structural analysis reveals that enantioselectivity arises from adaptive confinement within homochiral cavities, where subtle framework rearrangements and modulation of cavity volume amplify cooperative weak host-guest interactions. Systematic tuning of the molecular building blocks affords crystalline sponges capable of resolving challenging substrates such as the biobased green solvent 2-methyltetrahydrofuran, γ-valerolactone, and methylcyclohexanone isomers with enantiomeric excesses of up to 76%. These findings establish adaptive confinement in supramolecular crystalline sponges as a general mechanism for chiral discrimination in the solid state and provide a conceptual framework for enantioseparation beyond conventional crystallization-based approaches.
SN - 0002-7863
SN - 1520-5126
ER -