Interactions of phosphors and solid supports in room-temperature phosphorescence of aromatic compounds

General Information. 1 H NMR spectra were recorded with a JEOL JMN-500 (500 MHz) or a JEOL JMN-270 (270 MHz) spectrometer using CDCl 3 and acetone-d 6 as a solvent. Chemical shifts are reported in parts per million (δ) downfield from internal tetramethylsilane. 13 C NMR spectra were recorded with a JEOL JMN-270 (67.5 MHz) or a JEOL JMN-500 (125 MHz). Mass spectra were obtained on a Shimazu GCMS-QP 5050A instrument. Infrared spetra were obtained on a JASCO FT/IR-5300 spectrometer. Absorptions are reported in reciprocal centimeters. All products are known compounds and were identified by spectral data with comparison of literature data. General Procedure for Phase-Vanishing Bromination of Alkenes (Table 1, entry 1; Method A).Bromine (2 mmol, 320 mg) was added slowly to FC-72 (1.5 mL) in a test tube (13 mmφ x 105 mm) with a septum by using a glass pipette and then cyclohexene (2 mmol, 164 mg) in hexane (1.5 mL) was added slowly, forming three layers. The test tube was covered with aluminum foil in order to shield the reaction from light and kept at room temperature. After 2 days, the bromine layer disappeared and the fluorous layer recovered transparency. The hexane layer was taken up with a pipette. Then, additional hexane (2 mL x 4) was placed on the residual FC-72 layer, followed by decanting off. The combined hexane layer was washed with aqueous 2% Na 2 S 2 O 3 (30 mL) and water (30 mL), dried over MgSO 4 , and concentrated. Purification by a short column chromatography on silica gel with hexane gave trans-1,2-dibromocyclohexane (1.62 mmol, 392 mg) in 81% yield. General Procedure for Phase-Vanishing Bromination of Alkenes (Table 1, entry 2; Method B).Bromine (2.1 mmol, 335 mg) was added slowly to FC-72 (1.5 mL) in a test tube (13 mmφ x 105 mm) with a septum by using a glass pipette and then cyclohexene (2 mmol, 164 mg) in hexane (1.5 mL) was added slowly, forming three layers. The test tube was covered with aluminum foil in order to shield the reaction from light and kept at room temperature. Gentle stirring of the bromine layer using a magnetic stirrer was carried out, taking care not to mix the three layers. After 4 h, the bromine layer disappeared. The hexane layer was taken up with a pipette. Then, additional hexane (2 mL x 4) was placed on the residual FC-72 layer, followed by decanting off. The combined hexane layer was washed with aqueous 2% Na 2 S 2 O 3 (30 mL) and water (30 mL), dried over MgSO 4 , and concentrated. Purification by a short column chromatography on silica gel with hexane gave trans-1,2-dibromocyclohexane (1.8 mmol, 435 mg) in 90% yield.

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“…. 1 H NMR (270MHz, CDCl 3 ) 18 δ 6.90 (d, 2H, J = 8.6 Hz), 7.31 (m, 1H), 7.40-7.55 (m, 6H); IR (KBr) 19…”

Section: -Phenylphenol (Scheme 2)mentioning

confidence: 99%

Phase‐Vanishing Reactions That Use Fluorous Media as a Phase Screen. Facile, Controlled Bromination of Alkenes by Dibromine and Dealkylation of Aromatic Ethers by Boron Tribromide.

et al. 2003

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“…In practice, however, so many analytes and so many types of surface have been used to produce analytically useful RIP phenomena, that any single, simple mechanistic explanation for the phenomenon seems unlikely. Only recently (18,19) have serious attempts been made to use other spectroscopic methods to study the state of the adsorbed molecules: it seems likely that photoacoustic spectrometry may have considerable value in this connection.…”

Section: Phosphorimetry On Solid Surfacesmentioning

confidence: 99%

Luminescence measurements on surfaces

Miller¹

1985

Pure and Applied Chemistry

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-The paper describes the applications of solid surface luminescence measurements in the fields of cryogenic and room temperature phosphorescence, fluorescence immunoassays, and other areas. In many examples highly specific and sensitive assays are obtained by combining luminescence measurements with thin layer chromatography, and other laminar methods such as electrophoresis. Thin layer phosphorimetry is a promising approach, and may encourage the development of phosphorescent labels analogous to the currently common fluorescent labels. Several useful qualitative applications of surface luminescence have also been described, including the identification of glass samples, and the inclusion of phosphorescent and fluorescent markers on postage stamps and related materials.

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“…Virtually the entire laser beam (exclusing Fresnel losses, which are unavoidable) can be readily focused into a tiny spot inside the capillary orifice. Excellent sample selectivity and sensitivity have been reported for absorption (7), fluorescence (8,9), light scattering (70), refractive index (2, 77), and thermal lens (12) methods employing coherent laser light. Unfortunately, due to their relatively high degree of sophistication, laser-based detection methods are primarily suitable for research-oriented laboratories.…”

Section: Introductionmentioning

confidence: 99%

“…It has also been demonstrated that solid substrates are useful for the analysis of PAHs with both room-temperature and low-temperature phosphorescence spectrometry (1, 7-10). For example, RTP has been observed at the 200-ng level for certain phenols, hydroxynaphthalenes, and hydroxybiphenyls (7). However, a limitation of analytical RTP spectrometry is that the phosphorescence peaks are often broad and structureless, and sample separation procedures are often required for multicomponent analysis.…”

mentioning

confidence: 99%

Laser-induced phosphorescence spectrometry of halogenated naphthalene derivatives prepared in vapor-deposited parent molecule matrices

Pace¹,

Maple²

1989

Anal. Chem.

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Interactions of phosphors and solid supports in room-temperature phosphorescence of aromatic compounds

Cited by 39 publications

References 35 publications

Phase‐Vanishing Reactions That Use Fluorous Media as a Phase Screen. Facile, Controlled Bromination of Alkenes by Dibromine and Dealkylation of Aromatic Ethers by Boron Tribromide.

Phase‐Vanishing Reactions That Use Fluorous Media as a Phase Screen. Facile, Controlled Bromination of Alkenes by Dibromine and Dealkylation of Aromatic Ethers by Boron Tribromide.

Luminescence measurements on surfaces

Laser-induced phosphorescence spectrometry of halogenated naphthalene derivatives prepared in vapor-deposited parent molecule matrices

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