Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril: A new fluorescent host for detection of catechol and dopamine

Vladimir Sindelar, Mabel A. Cejas, Françisco M. Raymo, Weizhong Chen, Samantha E. Parker, Angel E. Kaifer

Research output: Contribution to journalArticle

154 Scopus citations

Abstract

The formation of a highly stable inclusion complex between 2,7-dimethyldiazapyrenium (Me2DAP2+) and the cucurbit[8]uril host (CB8) was demonstrated by X-ray crystallography; MALDI-TOF mass spectrometry; and 1H NMR, electronic absorption, and emission spectroscopy. The equilibrium association constant was determined to be 8.9(±0.2) × 105Lmol-1 from UV-visible data and 8.4(±1.5) × 105Lmol-1 from fluorescence data. The Me2DAP2+·CB8 inclusion complex acted as a host to bind compounds containing aromatic π-donor moieties (D), such as catechol and dopamine. This point was demonstrated by 1H NMR spectroscopy, and electrochemical and emission measurements. Fluorescence detection of the Me2DAP2+·D·CB8 ternary complexes was evident in aqueous solution and on the surface of silica particles, to which fluorescent diazapyrenium units had been covalently immobilized.

Original languageEnglish (US)
Pages (from-to)7054-7059
Number of pages6
JournalChemistry - A European Journal
Volume11
Issue number23
DOIs
StatePublished - Nov 18 2005

Keywords

  • Charge-transfer complexes
  • Cyclic voltammetry
  • Fluorescence
  • Host-guest systems
  • Sensors

ASJC Scopus subject areas

  • Chemistry(all)

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