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

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Original title:Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril: A new fluorescent host for detection of catechol and dopamine
Authors:Vladimír Šindelář, Mabel A Cejas, Francisco M Raymo, Weizhong Chen, Samantha E Parker, Angel E Kaifer
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Original language:English
Field:Macromolecular chemistry
Type:Article in Periodical
Keywords:cucurbiturils; self-assembly

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 crystallog.; MALDI-TOF mass spectrometry; and 1H NMR, electronic absorption, and emission spectroscopy. The equil. assocn. const. was detd. to be 8.9(ą0.2) 105 L mol-1 from UV-visible data and 8.4(ą1.5) 105 L mol-1 from fluorescence data. The Me2DAP2+CB8 inclusion complex acted as a host to bind compds. contg. arom. p-donor moieties (D), such as catechol and dopamine. This point was demonstrated by 1H NMR spectroscopy, and electrochem. and emission measurements. Fluorescence detection of the Me2DAP2+DCB8 ternary complexes was evident in aq. soln. and on the surface of silica particles, to which fluorescent diazapyrenium units had been covalently immobilized.