Cyclic peroxides. 59. On the mechanism of the rubrene-enhanced chemiluminescence of .alpha.-peroxylactones

Adam, Waldemar; Cueto, Omar; Yany, Faris

doi:10.1021/ja00476a074

Cited by 22 publications

(5 citation statements)

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“…Wagner et al have synthesized several ferrocene derivatives 11 via cross-coupling reaction as key step using palladium acetate. Various polycyclic hydrocarbons have been studied extensively with regard to fluorescence, [12][13][14] electrochemiluminescence, [15][16][17] enhanced chemiluminescence, 18,19 photoconductivity 20 and photooxidation 21 properties. Recent approach towards the synthesis of heterocyclic rubicene analogs via the ring-closer of 9,10diheteroarylanthracenes with Pd-catalyst is much simpler and gives good yield.…”

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confidence: 99%

Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Kotha¹,

Ghosh²,

Deodhar³

2004

Synthesis

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Synthesis of various 9,10-diarylanthracene derivatives via bis-Suzuki-Miyaura cross-coupling reaction as a key step is described. Availability of the 9,10-dithienylanthracenes derivatives where the thiophene unit is present in the molecule (e. g. 11, 12, 14) may provide an easy access to novel polymer and/or dendrimer preparation. In addition, we have synthesized unsymmetrical 9,10-diarylanthracene derivatives 20-25 by the Suzuki-Miyaura crosscoupling reaction, which are difficult to prepare by other transition metal-catalyzed cross-coupling reactions.

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confidence: 99%

Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Kotha¹,

Ghosh²,

Deodhar³

2004

Synthesis

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“…The reverse effect was observed by introduction of bromine substituent on the phenyl group. These results may be explained by the new concept recently developed by Schuster et al ('CIEEL' mechanism, Koo and Schuster, 1977b;Koo et al, 1978;Schmidt and Schuster, 1978;Adam et a/., 1978) and by McCapra (1977), although singlet quantum yields (4:) do not obey expectations from this concept, possibly and is known to have strong electron-donating abi-because of some unknown quenching factors. My, preferable to the formation of singlet excited state Very interestingly, dioxetane 10 gives on decomporather than triplet (Baumstark ef a/., 1976; Lee et a/., sition in dichloromethane a visible light emission cen-1976;McCapra et al, 1977).…”

Section: Resultsmentioning

confidence: 96%

Studies on Aminodioxetanes as a Model of Bioluminescence Intermediates. 1‐(1‐methyl‐3‐indolyl)‐6‐phenyl‐2,5,7,8‐tetraoxabicyclo[4,2,0]octane, an Aminodioxetane Resulting in Efficient Ultraviolet and Exciplex Chemiluminescence*

Nakamura

Gotot

1979

Photochem & Photobiology

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Abstract— The title aminodioxetane prepared by photooxygenation of 2–(l‐methyl‐3‐indolyl‐3‐phenyl‐1,4‐dioxene is fairly stable at −46°C and gives on warming to room temperature an ultraviolet light at Λmax 320 nm, which corresponds to 377kJ/mol; the highest energy ever observed among the efficient chemiluminescent compounds. The efficiency of chemiluminescence and excited singlet molecule formation in n‐hexane were 3.6% and at least 50%, respectively. Substitution and solvent effects suggest polar nature of the transition state as expected from the ‘CIEEL’ mechanism. In polar solvents, the dioxetane gives visible light (Λmax 400 nm in dichloromethane) as well as the UV light; the former being quenched by methanol. This is interpreted in terms of an intramolecular exciplex formation between the indole and phenyl groups. This is the first example of an intramolecular exciplex produced by the dioxetane decomposition.

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“…The efficiency of CIEEL reactions is governed by the magnitude of the oxidation potential. In fact, the intensity of light emitted during a CIEEL reaction reduces exponentially with an increase in oxidation potential. − ,, From extrapolation of the ln(light intensity) vs oxidation potential graph from o -xylylene peroxide 7 as an example, CIEEL light emission from DBA would be expected to be approximately 62 times less than that of DPA, when the greater fluorescence efficiency of DPA 49 is taken into account. The contribution to CL emission from a CIEEL mechanism will therefore be insignificant from DBA compared to DPA.…”

Section: Resultsmentioning

confidence: 99%

“…Hence, comparisons can be made between the data. Various authors [7][8][9][10]43,44 have demonstrated that DPA and other easily oxidizable polyaromatic hydrocarbons are capable of undergoing CIEEL reactions with various peroxides. Analysis of eq 6 indicates that if the CL activator concentration is constant, then the DPA I CLtime profile will be proportional to the hydroperoxide concentration.…”

Section: ∆Qmentioning

confidence: 99%

Energy Transfer and Activated Chemiluminescence during Thermal Oxidation of Polypropylene: Evidence for Chemically Induced Electron Exchange Luminescence

2001

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The mechanism of chemiluminescence (CL) during thermal oxidation of polypropylene (PP) was probed by doping PP with an energy acceptor (9,10-dibromoanthracene [DBA]) and a chemiluminescence (CL) activator (9,10-diphenylanthracene [DPA]). Doping PP with DBA had little effect on the shape of the CL intensity (I CL)−time profile. This suggests that energy transfer from triplet states is probably not significant in the scheme of PP CL. However, the CL activator (DPA) had a significant effect on the shape and intensity of the I CL−time profile. In the absence of DPA, the I CL−time profile matches the profile for the formation of carbonyl-containing oxidation products from FTIR-emission spectra. In contrast, in the presence of DPA, it was the integrated DPA I CL−time profile which matched the oxidation product profile, indicating that now I CL was proportional to the hydroperoxide concentration. It is suggested that peroxides formed during PP oxidation are capable of reacting with DPA to produce chemically induced electron exchange luminescence (CIEEL). It is also suggested that CL from undoped PP, i.e., direct CL, may also occur by a CIEEL mechanism. This mechanism is believed to involve the reaction of PP peroxides with an easily oxidizable luminescent oxidation product. For the detector system used in this study the majority of light emitted is consistent with reactions between acyl peroxides and α,β-unsaturated carbonyls. The consequences of this mechanism are that the I CL−time curve measured during the oxidation of PP may reflect either the hydroperoxide profile or the oxidation product profile depending on the spectral wavelength analyzed or the state of purity of the polymer.

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Cyclic peroxides. 59. On the mechanism of the rubrene-enhanced chemiluminescence of .alpha.-peroxylactones

Cited by 22 publications

References 0 publications

Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Synthesis of Symmetrical and Unsymmetrical 9,10-Diarylanthracene Derivatives via Bis-Suzuki-Miyaura Cross-Coupling Reaction

Studies on Aminodioxetanes as a Model of Bioluminescence Intermediates. 1‐(1‐methyl‐3‐indolyl)‐6‐phenyl‐2,5,7,8‐tetraoxabicyclo[4,2,0]octane, an Aminodioxetane Resulting in Efficient Ultraviolet and Exciplex Chemiluminescence*

Energy Transfer and Activated Chemiluminescence during Thermal Oxidation of Polypropylene: Evidence for Chemically Induced Electron Exchange Luminescence

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