Intramolecular energy transfer between the saturated amine and carbonyl chromophores

Halpern, Arthur M.; Walter, Robert B.

doi:10.1016/0009-2614(74)85327-3

Cited by 11 publications

(8 citation statements)

References 11 publications

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“…This hypothesis is supported by the observation that carbonyl fluorescence is observed not only upon excitation into the x* n transition (313 nm), but also upon irradiation at 238 nm (i.e., by exciting the amine chromophore). Moreover, it was determined quantitatively that the intramolecular energy transfer from the 238-nm populated state (excited amine) to the carbonyl x* n state was very efficient (see ref 5).…”

Section: Resultsmentioning

confidence: 99%

“…3 Only recently have the spectroscopic and photophysical properties of trialkylamines been investigated,4 and a study of the fluorescence of an amino ketone has been reported. 5 The bicyclic -amino ketone, l-azabicyclo[2.2.2]octan-3-one (1), has ben found to exhibit fluorescence characteristic of the ketone group, irrespective of whether excitation was into the amine or ketone transition.5 Intramolecular energy transfer was invoked to explain this result. The data also indicated the absence of ground-state interaction between the nitrogen lone pair and the carbonyl moiety.…”

mentioning

confidence: 99%

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Photophysical properties of .beta.-amino ketones. Investigation of tropinone, N-methyl-4-piperidone, and 1-diethylamino-3-butanone

Halpern¹,

Lyons²

1976

J. Am. Chem. Soc.

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Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Photophysical properties of .beta.-amino ketones. Investigation of tropinone, N-methyl-4-piperidone, and 1-diethylamino-3-butanone

Halpern¹,

Lyons²

1976

J. Am. Chem. Soc.

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“…The fluorescence efficiency (φF) of adamantanone is 5.2*10 -3 (ref. 28), which is high for an aliphatic ketone (φF acetone = 9.4*10 -4 ) (ref. 28,29).…”

Section: Introductionmentioning

confidence: 99%

“…28), which is high for an aliphatic ketone (φF acetone = 9.4*10 -4 ) (ref. 28,29). As it is related to φF, τ for S1adamantanone is also long for an alkanone (τS1 is 8*10 -9 s in CH3CN (ref.…”

Section: Introductionmentioning

confidence: 99%

Functionalized adamantylideneadamantane 1,2-dioxetanes: investigations on stable and inherently chemiluminescent compounds as a tool for clinical analysis

Hummelen¹,

Luider²,

Wynberg³

1987

Pure and Applied Chemistry

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Photophysical and thermodynamic properties of adamantylideneadamantane 1,2-dioxetane (1) and some functionalized derivatives, useful as thermochemiluminescent labels, are summarized. The emission of light from these compounds is stimulated simply by thermal activation. The low fluorescence efficiency of S1-adamantanone, the emitting product, causes the chemiluminescence efficiency to be moderate (φCL = 10 -4 ). The quantum efficiency of chemiluminescence φCL can be increased effectively through radiationless energy transfer to a fluorescent acceptor. The donor acceptor pair 1 and 9,10diphenylanthracene (DPA) is investigated in terms of Förster's theory. Proteins, labeled with derivatives of both 1 and DPA show increased thermochemiluminescent specific activity, in accord with this theory. Upon complexation with cyclodextrins, the evaporation of 1 and its derivatives at 240°C is inhibited. These complexes show a perfect dose-response linearity over a large range of concentration. Complexation also increases the reproducibility of chemiluminescence detection. Association constants for 1 and a derivative with both βand γ-cyclodextrin are presented.

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“…5 . lo-' in cyclohexane [16], both of which are independent of temperature [17]. By using this last value, which is appropriate for I-phenyldecane, a value of ca.…”

Section: Chemiluminescence Quantum Yields (#Icl) Carefully Weighed Smentioning

confidence: 99%

Thermolysis and Chemiluminescence of Monocyclic 1,2,4‐Trioxan‐5‐ones

Jefford

Josso

Vicente

et al. 1994

Helvetica Chimica Acta

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The 3,6-substituted 1,2,4-trioxan-S-ones 11-14, on heating to 170-200", underwent unimolecular thermolysis to generate electronically excited singlet ketones with an efficiency of cu. 0.2 %. The chemiluminescence quantum yields (kL) depended on the nature of the 6-subst1tuents and increased linearly with temperature. The Arrhenius activation energies were obtained by measuring the rate of decay of luminescence and determined as 22.9, 30.4, 35.6, and 34.2 kcal/mol for 11-14, respectively.Step analysis of the chemiluminescence of 14 afforded an average activation energy of 44.3 kcal/mol. This latter result is explicable in terms of two decomposition paths, higher and lower in energy, leading to excited and 'dark' products, respectively. The thermolysis of trioxanones 12-14 lacking a H-atom at the 6-position is interpreted as involving successive rupture of the peroxide bond, excision of ketone at the 3-substituted end, and loss of CO,, to finally produce ketone originating from the 6-position (see Scheme 4 ) .

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Intramolecular energy transfer between the saturated amine and carbonyl chromophores

Cited by 11 publications

References 11 publications

Photophysical properties of .beta.-amino ketones. Investigation of tropinone, N-methyl-4-piperidone, and 1-diethylamino-3-butanone

Photophysical properties of .beta.-amino ketones. Investigation of tropinone, N-methyl-4-piperidone, and 1-diethylamino-3-butanone

Functionalized adamantylideneadamantane 1,2-dioxetanes: investigations on stable and inherently chemiluminescent compounds as a tool for clinical analysis

Thermolysis and Chemiluminescence of Monocyclic 1,2,4‐Trioxan‐5‐ones

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