Chemiluminescence Involving Peroxide Decompositions

McCapra, Frank; Richardson, Donald G.; Chang, Yew C.

doi:10.1111/j.1751-1097.1965.tb09300.x

Cited by 67 publications

(29 citation statements)

References 24 publications

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“…McCapra and Chang investigated light emitting reactions with different 2,3-disubstituted indoles and their 3-hydroperoxide derivatives, proposing a mechanism that explains the observed chemiluminescence and which is consistent with Witkop's mechanistic proposals for that type of reaction (Scheme 14) [30][31]. The deprotonated amide group 69*, that is formed by decomposition of the cyclic peroxide, slowly relaxes from its excited state and functions as a transmitter for the chemiluminescence reaction.…”

Section: Oxidation With Oxygenmentioning

confidence: 55%

The Witkop-Winterfeldt-Oxidation of Indoles

Mentel¹,

Breinbauer

2007

COC

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In the early 1950s Witkop described in a series of papers that oxidation of indoles with a variety of oxidation reagents leads to the formation of quinolones. The mechanism of this reaction involves the oxidative cleavage of the 2,3-double bond of the indole moiety (Witkop-oxidation) followed by a Camps-cyclization forming the quinolone ring. Winterfeldt identified conditions which allow a one pot Witkop-oxidation/Camps-cyclization sequence and applied this strategy for the synthesis of pyrrolo[2,3-c]quinolones starting from 1,2,3,4-tetrahydro--carbolines. This review gives a comprehensive description of all described examples of this reaction including a definition of scope and limitations and a discussion of the mechanism of this transformation.

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Section: Oxidation With Oxygenmentioning

confidence: 55%

The Witkop-Winterfeldt-Oxidation of Indoles

Mentel¹,

Breinbauer

2007

COC

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“…Theoretical results have indicated that charge‐transfer processes should also be observed for CL systems containing no electron‐rich moiety . Moreover, the presence of oxidizable electron‐rich moieties are insufficient for the efficient formation of singlet excited states, in both intra‐ and intermolecular CL reactions …”

Section: The Molecular Mechanisms Of Chemiluminescencementioning

confidence: 99%

Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review

2016

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Photodynamic therapy (PDT) of cancer is known for its limited number of side effects, and requires light, oxygen and photosensitizer. However, PDT is limited by poor penetration of light into deeply localized tissues, and the use of external light sources is required. Thus, researchers have been studying ways to improve the effectiveness of this phototherapy and expand it for the treatment of the deepest cancers, by using chemiluminescent or bioluminescent formulations to excite the photosensitizer by intracellular generation of light. The aim of this Minireview is to give a précis of the most important general chemi-/bioluminescence mechanisms and to analyze several studies that apply them for PDT. These studies have demonstrated the potential of utilizing chemi-/bioluminescence as excitation source in the PDT of cancer, besides combining new approaches to overcome the limitations of this mode of treatment.

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“…We had earlier 22 chosen certain acridine derivatives as an easily studied series of chemiluminescent compounds. This series would appear to be among the least ambiguous and best understood of the examples of organic chemiluminescence at the present time.…”

Section: Chemiluminescence From Peroxide Decompositionmentioning

confidence: 99%

The chemiluminescence of organic compounds

McCapra¹

1970

Pure and Applied Chemistry

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The chemiluminescence of organic compounds in solution is briefly surveyed with some emphasis on the mechanisms which result in relatively efficient population of an excited state of a product molecule. This is done in terms of the relation l/J = l/Jc x l/JE x l/JF with particular reference to peroxide compositions. INTRODUCTIONThe study of chemiluminescence mechanism in a persistent and systematic fashion is an activity largely confined to the last decade. This is not surprising when one considers that the problems associated with ground-excited state interactions must be multiplied by the complexities of a vigoraus oxidative reaction for a full description of a chemiluminescent reaction. A general survey of the phenomenon discloses that, with almost no exceptions, oxidation is involved, the mechanism ranging from the relative simplicity of an electron transfer reaction to the confusion of a many step, bond cleavage process. The excitation step in certain bioluminescent reactions is of particular interest as an example of the latter kind. Although luminescence in the gas phase has been comparatively weil understood for a long time, there are various reasons why the problern of chemiluminescence in solution must be approached differently. All gas phase reactions emitting light involve di-or tri-atomic molecules and often atom recombination. The restriction of the degrees of freedom in small molecules and the near absence of collision in the gas phase Ieads to a non-equilibrium distribution of the energy derived from the exotherrnie reaction. If one assumes that the reactants in an exotherrnie reaction in solution are, within the lifetime of an excited species, in equilibrium with the surrounding solvent, then it is obvious that in this case vibrational energy, no matter how great, is an unlikely source of electronic excitation. Thus of the various mechanisms for organic chemiluminescence, electron transfer is particularly attractive. Conversely, there is no weil proven instance ofthe emission oflight from a radical recombination reaction in solution, although the bonds formed in such a process usually release more than sufficient energy to populate an electronically excited state. A further consequence of the conditions under which most organic chemiIuminescent reactions occur is the observation that emission is from the first excited singlet state, the triplet state being easily quenched. However, there

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Chemiluminescence Involving Peroxide Decompositions

Cited by 67 publications

References 24 publications

The Witkop-Winterfeldt-Oxidation of Indoles

The Witkop-Winterfeldt-Oxidation of Indoles

Chemiluminescence and Bioluminescence as an Excitation Source in the Photodynamic Therapy of Cancer: A Critical Review

The chemiluminescence of organic compounds

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