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Rigid, biconical hydrogen-bonded dimers that strongly encapsulate cationic guests in solution and the solid state† † Electronic supplementary information (ESI) available: Synthetic procedures and characterization data of all new compounds; details of solution spectroscopic/crystallographic characterization of dimer and host–guest complexes; details of calculations and electrostatic potential maps. CCDC 2070238. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/d1sc01802g

ABSTRACT: The octol of a new rigid, tetraarylene-bridged cavitand was investigated for self-assembly behaviour in solution. 1H and DOSY NMR spectroscopic experiments show that the cavitand readily dimerizes through an unusual seam of interdigitated hydrogen-bonds that is resistant to disruption by polar co-solvents. The well-defined cavity encapsulates small cationic guests, but not their neutral counterparts, restricting the conformation of sequestered tetraethylammonium in solution and the solid state. A robust, dimeric capsule forms quantitatively in low-polarity solvents via a seam of 8 hydrogen bonds. The resulting electron-rich cavity selectively binds small organic cations over neutral counterparts.

SUBMITTER: Smith J

PROVIDER: S-EPMC8442710 | biostudies-literature |

REPOSITORIES: biostudies-literature

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