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 › peer-review

161 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)

Access to Document

10.1002/chem.200500917

Cite this

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 › peer-review

@article{82940ae0dbe64cc2b7b59ff5e2f0a861,

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

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.",

keywords = "Charge-transfer complexes, Cyclic voltammetry, Fluorescence, Host-guest systems, Sensors",

author = "Vladimir Sindelar and Cejas, {Mabel A.} and Raymo, {Fran{\c c}isco M.} and Weizhong Chen and Parker, {Samantha E.} and Kaifer, {Angel E.}",

year = "2005",

month = nov,

day = "18",

doi = "10.1002/chem.200500917",

language = "English (US)",

volume = "11",

pages = "7054--7059",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "23",

}

TY - JOUR

T1 - Supramolecular assembly of 2,7-dimethyldiazapyrenium and cucurbit[8]uril

T2 - A new fluorescent host for detection of catechol and dopamine

AU - Sindelar, Vladimir

AU - Cejas, Mabel A.

AU - Raymo, Françisco M.

AU - Chen, Weizhong

AU - Parker, Samantha E.

AU - Kaifer, Angel E.

PY - 2005/11/18

Y1 - 2005/11/18

N2 - 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.

AB - 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.

KW - Charge-transfer complexes

KW - Cyclic voltammetry

KW - Fluorescence

KW - Host-guest systems

KW - Sensors

UR - http://www.scopus.com/inward/record.url?scp=27944477253&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=27944477253&partnerID=8YFLogxK

U2 - 10.1002/chem.200500917

DO - 10.1002/chem.200500917

M3 - Article

C2 - 16175642

AN - SCOPUS:27944477253

VL - 11

SP - 7054

EP - 7059

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

SN - 0947-6539

IS - 23

ER -

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

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this