Cucurbit[7]uril-Encapsulation-Controlled Supramolecular Photoproduct and Radical Fluorescence Emission

Chemistry. 2022 Nov 2;28(61):e202202056. doi: 10.1002/chem.202202056. Epub 2022 Sep 2.

Abstract

Herein, a host-guest interaction-controlled photoproduct created by using cucurbit[7]uril (Q[7])-based pseudorotaxane structures is reported. The assembly exhibited controlled behavior towards the reduction of the ethylene (C=C) bond in the tetrakis(pyridin-4-yl)ethylene (TPyE) guest molecule under UV light irradiation. This can be attributed to the Q[7] encapsulation masking the four pyridinium arms of the guest, which inhibits planarization of the TPyE core to form the cyclization product. In particular, the strong affinity of Q[7] for the butyl-substituted guest (TPyE-4C) led to an unusual radical fluorescence emission of the photoirradiation-triggered intermediate of the guest molecule being observed in aqueous solution. This work provides a valuable paradigm and new insight for macrocycle-based host-guest interactions in supramolecular catalysis and luminescent radical materials.

Keywords: host-guest complexes; macrocycles; photocatalysis; radical fluorescence.

MeSH terms

  • Bridged-Ring Compounds* / chemistry
  • Ethylenes
  • Imidazoles* / chemistry
  • Spectrometry, Fluorescence

Substances

  • cucurbit(7)uril
  • Bridged-Ring Compounds
  • Imidazoles
  • Ethylenes