Controlled oligomeric guest stacking by cucurbiturils in water - Archive ouverte HAL Access content directly
Journal Articles Organic & Biomolecular Chemistry Year : 2023

Controlled oligomeric guest stacking by cucurbiturils in water

Fengbo Liu
  • Function : Author
  • PersonId : 1311607
Amine Kriat
  • Function : Author
Roselyne Rosas
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  • PersonId : 1311608
David Berge-Lefranc
Didier Gigmes
Olivier Siri
Simin Liu
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  • PersonId : 1085495
Anthony Kermagoret
David Bardelang

Abstract

Previously, we have reported a guest molecule containing a viologen (V), a phenylene (P) and an imidazole (I) fragment (VPI) forming a host:guest 2:2 complex with cucurbit[8]uril (CB[8]) and an unprecedented 2:3 complex with cucurbit[10]uril (CB[10]). To better address the structural features required to form these complexes, two VPI analogues were designed and synthesized, the first with a tolyl (T) group grafted on the V part (T-VPI), and the second with a naphthalene (N) fused on the imidazole (I) part (VPI-N). While VPI-N afforded a discrete well-defined 2:2 complex with CB[8] and a 2:3 complex with CB[10], T-VPI organized also as a 2:2 complex with CB[8] but no well-defined complex was obtained with CB[10]. These complexes were studied by NMR notably DOSY, and allowed to estimate binding constants for 2:2 complex formation with CB[8] pointing to more stable 2:2 complexes with more hydrophobic guests. UV-vis and fluorescence spectroscopies confirmed complex formation, suggesting host-stabilized charge-transfer interactions. Therefore, the simple addition of CB[8] or CB[10] enabled to control the level of guest stacking (dimer or trimer) using relevant pairs of synthetic hosts through spontaneous, host:guest quaternary or quinary self-assembly.
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Dates and versions

hal-04294802 , version 1 (20-11-2023)

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Fengbo Liu, Amine Kriat, Roselyne Rosas, David Berge-Lefranc, Didier Gigmes, et al.. Controlled oligomeric guest stacking by cucurbiturils in water. Organic & Biomolecular Chemistry, 2023, ⟨10.1039/D3OB01723K⟩. ⟨hal-04294802⟩
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