Room-temperature phosphorescence of polynuclear aromatic hydrocarbons in cyclodextrins

Scypinski, Stephen; Love, L. J. Cline.

doi:10.1021/ac00267a005

Cited by 240 publications

(90 citation statements)

References 19 publications

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“…Under deoxygenated solvent conditions, CDs can enhance the room temperature phosphorescence (RTP) of various compounds such as 6-bromo-2-naphthol derivatives [8][9][10][11], polynuclear aromatic hydrocarbons [12,13], or acid-base indicators such as neutral red [14]. In the case of some exceptional, well-protected complexes strong RTP signals can even be observed without deoxygenation [15].…”

Section: Introductionmentioning

confidence: 99%

Enantioselective detection of chiral phosphorescent analytes in cyclodextrin complexes

García-Ruiz

Scholtes

Ariese

et al. 2005

Talanta

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Inclusion complexes between camphorquinone (CQ) and cyclodextrins (CDs) in deoxygenated aqueous solutions are shown to exhibit relatively strong room temperature phosphorescence (RTP). Among the various CDs tested, ␣-CD showed the strongest RTP signals. Interestingly, these signals differed significantly for the two enantiomers of CQ; the phosphorescence lifetime of (+)-CQ was about four times longer than that of (−)-CQ, being 352 ± 16 and 89 ± 6 s, respectively. This enantiomeric selectivity is attributed to a difference in dissociation rates (competing with the radiative emission process) for the diastereoisomeric inclusion complexes dealt with, which have a 2:1 stoichiometry (␣-CD:CQ:␣-CD). Time-resolved RTP detection using different delay times enables the determination of the two enantiomers in a mixture without involving a separation technique. The minimum detectable fraction of (+)-CQ in a 2 mM sample was 13%.

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Section: Introductionmentioning

confidence: 99%

Enantioselective detection of chiral phosphorescent analytes in cyclodextrin complexes

García-Ruiz

Scholtes

Ariese

et al. 2005

Talanta

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“…Other photochemists were attracted quite early to this field of research and initiated studies, which were mostly photophysical in nature [7,8]. The key observation was that the formation of supramolecular complexes of analytes with cyclodextrins (CDs) resulted in an increase of their fluorescence quantum yield or even in the appearance of room temperature phosphorescence (RTP) [9][10][11][12]. This enhancement has been used to increase the sensitivity and the selectivity in both luminescence and chromatographic techniques [13][14][15].…”

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confidence: 99%

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Lerner¹,

Martín²

2000

Analusis

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Introduction Molecular luminescence of analytes in organized media or in supramolecular complexes of cyclodextrinsThe photophysical and photochemical behaviour of molecules complexed to cyclodextrins (CD) is generally different from their behaviour in solution. The first observations in the field were qualitative and were related to the increased stabilisation of labile molecules, mostly drugs, against photodegradation when complexed to natural cyclodextrins [1]. Complexation by CD's was then the preferred subject for those involved in supramolecular chemistry and drug vectorisation techniques [2] as well as in separation techniques [3][4][5]. Stabilization of a molecule against photochemical degradation is still very important in the field of pharmaceutical sciences. A recent example is the stabilisation of promazine as an inclusion complex with β-cyclodextrin [6]. Other photochemists were attracted quite early to this field of research and initiated studies, which were mostly photophysical in nature [7,8]. The key observation was that the formation of supramolecular complexes of analytes with cyclodextrins (CDs) resulted in an increase of their fluorescence quantum yield or even in the appearance of room temperature phosphorescence (RTP) [9][10][11][12]. This enhancement has been used to increase the sensitivity and the selectivity in both luminescence and chromatographic techniques [13-15].We will not say more about RTP with CDs as the subject will be developed in another contribution in the same issue of this Journal. However RTP is also observed in the solubilization of analytes in micellar colloïdal solutions and this field will be reviewed hereunder.These properties have been used to develop analytical techniques, which combine the selectivity of complexation with an enhanced emission [16][17][18][19]. In this way an improvement in the detection limits is obtained in many separation techniques such as HPLC, capillary electrophoresis (CE) or planar chromatography. Furthermore these molecular interactions allow to reveal or to stabilize new molecular forms or to turn species which are normally non-emitting into luminescent ones. All these aspects are reviewed hereunder after a short summary on the nature of the intermolecular interactions, which lie at the heart of these effects. Nature of the interactions between an analyte and a CD or a micelleWithout going into a thorough analysis of the origin of the interactions which exist between molecules in dense media which concern us here, it seems useful to recall the most important factors which should be taken into account when any type of luminescence, fluorescence or phosphorescence is involved.

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“…In order to demonstrate the applicability of the automated deoxygenation system to phosphorescence measurement, we used the inclusion complex formed with l-bromonaphthalene and 8-cyclodextrin. Cyclodextrin complexes have been shown to be somewhat insensitive to oxygen quenching (24). Nevertheless, the phosphorescence emission could be increased by 40% of the original intensity using the automated deoxygenation apparatus.…”

Section: J1mentioning

confidence: 99%

Automated sample deoxygenation for improved luminescence measurements

Rollie¹,

Patonay²,

Warner³

1987

Anal. Chem.

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Room-temperature phosphorescence of polynuclear aromatic hydrocarbons in cyclodextrins

Cited by 240 publications

References 19 publications

Enantioselective detection of chiral phosphorescent analytes in cyclodextrin complexes

Enantioselective detection of chiral phosphorescent analytes in cyclodextrin complexes

Luminescence in organized media and supramolecular interactions:physicochemical aspects and applications

Automated sample deoxygenation for improved luminescence measurements

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