<b>The Quenching Effect of Naphthalene on the Photoreduction of Benzophenone</b>

Moore, William M.; Ketchum, Marshall D.

doi:10.1021/ja00867a007

Cited by 86 publications

(44 citation statements)

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“…57 We are most grateful to Doctors A. The solvated electron in M T H F is reported to have a monotonically increasing absorption in the range 4000-13000 Aa58 In a separate experiment, irradiation of lumisantonin in the presence of 0.01 M biphenyl did not give rise to the characteristic spectrum of biphenylide anion Under these conditions, any electrons formed should have been scavenged by biphenyl.…”

Section: Methodsmentioning

confidence: 92%

The mechanism of the photochemical rearrangement of lumisantonin

Fisch¹,

Richards²

1968

J. Am. Chem. Soc.

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For PhzCO + hv + In conversions in excess of 50%, the reaction mixture at the end of the dark reaction will contain In, which will ultimately have to react with atmospheric oxygen upon admission of air. one can easily obtain quantum Yields of Ph2CO disappearance ranging from 1 to 2. The only case in which this quantum yield can be close to 2 is if the Abstract: Sensitization studies on the photolysis of lumisantonin together with a reinvestigation of its pyrolysis have yielded results which support a mechanism involving five discreet steps: (1) excitation; (2) intersystem crossing; (3) bond breaking; (4) electron demotion and relaxation to a dipolar state; (5) rearrangement. Photolysis at low temperature in a matrix allowed the trapping of a colored intermediate the lifetime and spectral characteristics of which are consistent with the postulated dipolar state. The possibilities of electron ejection from an excited state or reaction uia vibrationally excited ground states are discussed and considered to be unlikely in this system. or several years interest has centered on "ionic"

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Section: Methodsmentioning

confidence: 92%

The mechanism of the photochemical rearrangement of lumisantonin

Fisch¹,

Richards²

1968

J. Am. Chem. Soc.

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“…The solution contained tetradecane as the internal standard and was nitrogen purged. The benzophenonebenzhydrol system in benzene was used for the actinometry with a quantum yield of 0.74 (25). The solution was irradiated for 60-75 min resulting in 6-15% yields of 2.…”

Section: Quantum Yield Determirzatiorimentioning

confidence: 99%

The photoaddition of 1,3-diketonatoboron difluorides with benzene derivatives

Chow¹,

Ouyang²

1991

Can. J. Chem.

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The boron difluoride complexes of 2-acetylcyclohexanone, 2-acetylcyclopentanone, and acetylacetone (abbreviated as ACHBF2, ACPBF2, and AABF2) were irradiated in the presence of benzene to give the 1:1 adducts as the primary photoadducts; for certain BF2 complexes, toluene, chlorobenzene, benzonitrile, and methyl benzoate were also used as substrates. The 1,5-diketone photoadducts were assumed to form by a [2+2] photocycloaddition followed by cyclobutane opening and hydrolysis to give 1,2 adducts. They undergo a variety of secondary thermal reactions, probably acid catalyzed, to give enol ethers, enol acetates, acetophenones, and ketonylacetophenones. The efficiency of these secondary reactions determines the final products. Photoaddition with a monosubstituted benzene preferentially occurs at the 3,4 bond without regioselectivity. Under oxygen, ACHBF2 photolytically reacts with benzene to give a secondary oxidation product of a 10-membered cyclic alkylphe-none, which is proven by X-ray crystallographic analysis to have the benzene ring and carbonyl group in orthogonal orientation. It is shown that the singlet excited state ACHBF2 initiates the photoaddition, probably through the formation of the benzene exciplex, which could be detected by its emission. While the Stern–Volmer rates are small, the quantum yield of photoaddition products is as high as 0.12–0.19 under limiting conditions. Key words: [2+2] photocycloaddition, non-planar alkanophenone, macrocyclic alkanophenone, boron difluoride complexes, photoaddition to benzenes.

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“…Since the first report by Terenin and Ermolaev, benzophenone (BP)/naphthalene (NP) systems have been widely used as models to study inter-and intra-molecular singletsinglet and triplet-triplet energy transfer processes [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. Thus, Shizuka and coworkers have intensively investigated the sensitization of the NP triplet by BP, the behavior of the triplet-excited states of BP and NP and their interactions.…”

Section: Introductionmentioning

confidence: 99%

Fast transient absorption spectroscopy of the early events in photoexcited chiral benzophenone–naphthalene dyads

Pérez‐Ruiz¹,

Groeneveld²,

Stokkum³

et al. 2006

Chemical Physics Letters

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General rightsIt is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulationsIf you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: http://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. Download date: 10 May 2018This article was originally published in a journal published by Elsevier, and the attached copy is provided by Elsevier for the author's benefit and for the benefit of the author's institution, for non-commercial research and educational use including without limitation use in instruction at your institution, sending it to specific colleagues that you know, and providing a copy to your institution's administrator. All other uses, reproduction and distribution, including without AbstractPhotoinduced intra-molecular energy transfer in two ketoprofen(KP)-naproxol(NPX) diastereomers proceeds via two pathways. Very fast singlet-triplet energy transfer (k = 1.2 · 10 11 s À1 ) from KP to NPX occurs for a small percentage (6%) and the major pathway is triplet-triplet energy transfer (k $ 3 · 10 9 s À1 ). This was shown with femtosecond transient absorption spectroscopy and global and target analysis. Whereas the NPX triplet decay is strongly stereospecific (ratio of 1.6), the NPX triplet state formation for both dyads is very similar (ratio of 1 for the fast process and 1.2 for the slower process).

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The Quenching Effect of Naphthalene on the Photoreduction of Benzophenone

Cited by 86 publications

References 1 publication

The mechanism of the photochemical rearrangement of lumisantonin

The mechanism of the photochemical rearrangement of lumisantonin

The photoaddition of 1,3-diketonatoboron difluorides with benzene derivatives

Fast transient absorption spectroscopy of the early events in photoexcited chiral benzophenone–naphthalene dyads

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