Tightly-Twisted One-Handed Helical Tubular Ladder Polymers with π-Electron-Rich Cylindrical Helical Cavities for Chromatographic Enantioseparation

12 December 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Defect-free one-handed contracted helical tubular ladder polymers with a π-electron-rich cylindrical helical cavity were synthesized by alkyne benzannulations of the random-coil precursor polymers containing 6,6´-linked-1,1´-spirobiindane-7,7´-diol-based chiral monomer units. The resulting tightly-twisted helical tubular ladder polymers showed remarkably high enantioseparation abilities toward a variety of chiral hydrophobic aromatics with point, axial, and planar chiralities. The random-coil precursor polymer and analogous rigid-rod extended helical ribbon-like ladder polymer with no internal helical cavity exhibited no resolution abilities. The molecular dynamics simulations suggested that the π-electron-rich cylindrical helical cavity formed in the tightly-twisted tubular helical ladder structures is of key importance for producing the highly-enantioseparation ability, by which chiral aromatics can be enantioselectively encapsulated by specific π–π and/or hydrophobic interactions.


alkyne benzannulations
chiral recognition
ladder formation
helical cavities
spiro structures

Supplementary materials

Supporting Information
Full experimental details, characterizations of monomers and polymers, and additional supporting data


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