The Chemiluminescence of Lophine and Its Derivatives

White, Emil H.; Harding, Maurice J. C.

doi:10.1021/ja01078a062

Cited by 99 publications

(62 citation statements)

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“…Furthermore, the luminescence is barely modifed by oxygen, and hence it must arise from the excited singlet and/or a very short-lived triplet. This result is in agreement with previous reports that substituents of high electron affinity tend to decrease the photoemission quantum yield of aryl ketones (Adam and Cilento 1982;McCapra and Chang 1966;White and Harding 1964). In addition, p-nitrobenzophenone has been reported to exhibit rapid energy transfer from the nn* carbonyl triplet to the nn* nitro group triplet (Hautala and Mayer, 1977).…”

Section: Recombinationssupporting

confidence: 93%

Excited carbonyl formation in the combination and disproportionation of free radicals

Fuente¹,

Lissi²

1992

J. Biolumin. Chemilumin.

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The pyrolyisis of di-tert-butyl peroxyoxalate in the presence of para-substituted benzaldehydes produces almost quantitatively the corresponding p,p'-disubstituted benzils. The formation of these products is accompanied by chemiluminescence arising from excited triplets. From the quantum yield of excited triplet generation and the rate constants for the triplet photocleavage it is possible to obtain the change in Gibbs free energy associated with triplet formation. The values obtained are -5.6, -5.7 and -8.1 kcal/mol for benzil, p,p'-dimethylbenzil and p,p'-dimethoxybenzil, respectively. The pyrolysis of di-tert-butyl peroxyoxalate in the presence of isopropanol or benzoin leads to the formation of acetone and benzil. These products are generated in disproportionation processes involving the alpha-hydroxy radical produced by hydrogen abstraction. The luminescence observed in these reactions constitutes the first experimental indication of excited species generation in the disproportionation of uncorrelated free radicals.

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Section: Recombinationssupporting

confidence: 93%

Excited carbonyl formation in the combination and disproportionation of free radicals

Fuente¹,

Lissi²

1992

J. Biolumin. Chemilumin.

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“…[56] For both compounds, red chemiluminescence was observed in different solvents (%629 nm in DMSO and % 649 nm in water). This latter phenomenon gained attention from biolu-Scheme 2.…”

Section: Firefly Chemiluminescencementioning

confidence: 96%

Firefly Chemiluminescence and Bioluminescence: Efficient Generation of Excited States

Silva

2012

ChemPhysChem

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Firefly luciferase catalyzes a light-emitting reaction in which an excited-state product is formed. Both experimental and theoretical methodologies are used to study this system, and the reactions catalyzed by luciferase are relatively well characterized. However, the mechanism by which an excited-state product is formed is still unknown. This Minireview deals with the current understanding of firefly bioluminescence and chemiluminescence. Thermal decomposition of simple 1,2-dioxetanes is also discussed, due to their role in formation of the excited-state bioluminophore.

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“…The reaction completed within 4–6 h. Aromatic substituents containing electron‐donating as well as electron‐withdrawing groups underwent the elimination of oxygen facilely. In the case of unstable 1c , which is difficult to isolate, [2] 5c was consequently prepared by treating the mixture by the photooxidation of the corresponding imidazole with DMSO. In the cases of 1g , 1h , the mixtures with their isomers ( 1'g , 1'h ) were used to afford mixtures of 5g , 5h with their isomers ( 5'g , 5'h ), as shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

“…The chemiluminescent reactions of lophine hydroperoxides ( 1 ) have attracted considerable attention for many decades [1, 2]. Many studies have been reported [3] and these studies mainly focused on the chemiluminescence (CL) efficiency.…”

Section: Introductionmentioning

confidence: 99%

Preparation of 2,4,5‐triarylimidazol‐4‐ols and their stereoselective rearrangement by 1,5‐phenyl migration

Katoh

Zhang

et al. 2010

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).Lophine hydroperoxides underwent base-triggered 1,5-phenyl migration in DMSO to afford imidazolones in high yields, instead of amidines with chemiluminescence (CL). The corresponding imidazolols were believed to intermediates and they were successfully obtained by treating the peroxides with DMSO without the base. The diminished CL was because of the reduction of the hydroperoxides with DMSO. The imidazolols subsequently underwent smooth base-mediated rearrangement to afford imidazolones. Furthermore, the chiral imidazolols provided stereoselective imidazolones in high enantiomeric excess (>92%), which supported the mechanism of an intramolecular ring for the migration.

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The Chemiluminescence of Lophine and Its Derivatives

Cited by 99 publications

References 0 publications

Excited carbonyl formation in the combination and disproportionation of free radicals

Excited carbonyl formation in the combination and disproportionation of free radicals

Firefly Chemiluminescence and Bioluminescence: Efficient Generation of Excited States

Preparation of 2,4,5‐triarylimidazol‐4‐ols and their stereoselective rearrangement by 1,5‐phenyl migration

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