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

doi:10.1002/chem.200500917

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

Chemistry

Research output: Contribution to journal › Article

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 language	English (US)
Pages (from-to)	7054-7059
Number of pages	6
Journal	Chemistry - A European Journal
Volume	11
Issue number	23
DOIs	https://doi.org/10.1002/chem.200500917
State	Published - Nov 18 2005

Keywords

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

ASJC Scopus subject areas

Chemistry(all)

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10.1002/chem.200500917

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Sindelar, V., Cejas, M. A., Raymo, F. M., Chen, W., Parker, S. E., & Kaifer, A. E. (2005). Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril: A new fluorescent host for detection of catechol and dopamine. Chemistry - A European Journal, 11(23), 7054-7059. https://doi.org/10.1002/chem.200500917

Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril : A new fluorescent host for detection of catechol and dopamine. / Sindelar, Vladimir; Cejas, Mabel A.; Raymo, Françisco M.; Chen, Weizhong; Parker, Samantha E.; Kaifer, Angel E.

In: Chemistry - A European Journal, Vol. 11, No. 23, 18.11.2005, p. 7054-7059.

Research output: Contribution to journal › Article

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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.",

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