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Mechanistic organic photochemistry

About: Mechanistic organic photochemistry is a research topic. Over the lifetime, 626 publications have been published within this topic receiving 17267 citations. The topic is also known as: Mechanistic organic photochemistry.


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Journal ArticleDOI
28 Feb 2014-Science
TL;DR: A variety of reaction types have now been shown to be amenable to visible light photocatalysis via photoinduced electron transfer to or from the transition metal chromophore, as well as energy-transfer processes.
Abstract: Background Interest in photochemical synthesis has been motivated in part by the realization that sunlight is effectively an inexhaustible energy source.Chemists have also long recognized distinctive patterns of reactivity that are uniquely accessible via photochemical activation. However, most simple organic molecules absorb only ultraviolet (UV) light and cannot be activated by the visible wavelengths that comprise most of the solar energy that reaches Earth’s surface. Consequently, organic photochemistry has generally required the use of UV light sources. Visible light photocatalysis. ( A ) Transition metal photocatalysts, such as Ru(bpy) 3 2+ , readily absorb visible light to access reactive excited states. ( B ) Photoexcited Ru*(bpy) 3 2+ can act as an electron shuttle, interacting with sacrificial electron donors D (path i) or acceptors A (path ii) to yield either a strongly reducing or oxidizing catalyst toward organic substrates S. Ru*(bpy) 3 2+ can also directly transfer energy to an organic substrate to yield electronically excited species (path iii). bpy, 2,29-bipyridine; MLCT, metal-to-ligand charge transfer. Advances Over the past several years, there has been a resurgence of interest in synthetic photochemistry, based on the recognition that the transition metal chromophores that have been so productively exploited in the design of technologies for solar energy conversion can also convert visible light energy into useful chemical potential for synthetic purposes. Visible light enables productive photoreactions of compounds possessing weak bonds that are sensitive toward UV photodegradation. Furthermore, visible light photoreactions can be conducted by using essentially any source of white light, including sunlight, which obviates the need for specialized UV photoreactors. This feature has expanded the accessibility of photochemical reactions to a broader range of synthetic organic chemists. A variety of reaction types have now been shown to be amenable to visible light photocatalysis via photoinduced electron transfer to or from the transition metal chromophore, as well as energy-transfer processes. The predictable reactivity of the intermediates generated and the tolerance of the reaction conditions to a wide range of functional groups have enabled the application of these reactions to the synthesis of increasingly complex target molecules. Outlook This general strategy for the use of visible light in organic synthesis is already being adopted by a growing community of synthetic chemists. Much of the current research in this emerging area is geared toward the discovery of photochemical solutions for increasingly ambitious synthetic goals. Visible light photocatalysis is also attracting the attention of researchers in chemical biology, materials science, and drug discovery, who recognize that these reactions offer opportunities for innovation in areas beyond traditional organic synthesis. The long-term goals of this emerging area are to continue to improve efficiency and synthetic utility and to realize the long-standing goal of performing chemical synthesis using the sun.

1,859 citations

Book
01 Jan 1995
TL;DR: Spectroscopy in the visible and UV region absorption spectra of organic molecules optical activity principles of the quantum chemical description of photophysical and photochemical processes photophysical processes photochemical reaction models organic photochemistry as mentioned in this paper.
Abstract: Spectroscopy in the visible and UV region absorption spectra of organic molecules optical activity principles of the quantum chemical description of photophysical and photochemical processes photophysical processes photochemical reaction models organic photochemistry

944 citations

Book
01 Jan 1978
TL;DR: In this paper, a theory of molecular organic photochemistyr is presented, and a generalization of the Photochemistry of organic Molecules Index is presented for the first time.
Abstract: 1. Molecular Photochemistry of Organic Compounds: An Overview 2. Electronic, Vibrational, and Spin Configurations of Electronically Excited States 3. Transitions between States: Photophysical Processes 4. Radiative Transitions between Electronic States 5. Photophysical Radiationless Transitions 6. A Theory of Molecular Organic Photochemistyr 7. Energy Transfer and Electron Transfer 8. Mechanistic Organic Photochemistry 9. Photochemistry of Carbonyl Compounds 10. Photochemistry of Olefins 11. Photochemistry of Enones and Dienones 12. Photochemistry of Aromatic Molecules 13. Supramolecular Organic Photochemistry 14. Molecular Oxygen and Organic Photochemistry 15. A Generalization of the Photochemistry of Organic Molecules Index

732 citations

Book
01 Jan 2004
TL;DR: Kaupp and Kropp as mentioned in this paper proposed a 2+2-cyclobutane synthesis (2+2)-cycle synthesis (Liquid Phase): Introduction and Mechanistic Consideration, G.G.
Abstract: Photochemistry Cis-Trans Isomerization of Alkenes, J. Saltiel, D.F. Sears, Jr., D.-H. Ko, and K.-M. Park Photorearrangement and Fragmentation of Alkenes, P.J. Kropp (2+2)-Cyclobutane Synthesis (Liquid Phase): Introduction and Mechanistic Consideration, G. Kaupp Cyclobutane Synthesis in the Solid Phase: Introduction and Mechanistic Considerations, G. Kaupp Photochemical Synthesis of Cage Compounds: Propellaprismanes and their Precursors, R. Gleiter and B. Treptow Copper(I) Catalyzed Intra- and Intermolecular Photocycloaddition Reactions of Alkenes, K. Langer and J. Mattay Photoreactions of Alkenes in Protic Media, P.J. Kropp The p-Cyclopropene Rearrangements, H.E. Zimmerman Diene/Cyclobutene Photochemistry, W.J. Leigh Photochemistry of Acyclic 1,3,5-Trienes and Related Compounds, W.H. Laarhoven and H.J.C. Jacobs Photochemistry of Vitamin D and Related Compounds, H.J.C. Jacobs and W.H. Laarhoven Photochemistry of Polyenes Related to Vitamin A, R.S.H. Liu Fulgides and Related Systems, H.G. Heller The Di-p-Methane Rearrangement, H.E. Zimmerman Photorearrangements of Benzobarrelenes and Related Analogues, C.-C. Liao and P.-H. Yang The Photochemistry of Dibenzobarrelene (9,10-Ethenoanthracene) and its Derivatives, J.R. Scheffer and J. Yang Valence Isomerization Between Norbornadiene and Quadricyclane Derivatives-A Solar Energy Storage Process, K. Maruyama and Y. Kubo Ring Isomerization of Benzene and Naphthalene Derivatives, A. Gilbert Phototransposition and Photo-Ring Contraction Reactions of 4-Pyrones and 4-Hydroxypyrylium Cations, J.W. Pavlik Photochemical Aromatic Substitution, J. Cornelisse Photochemical Reactions of Arenes with Amines, N.J. Bunce Intra- and Intermolecular Cycloadditions of Benzene Derivatives, P.A. Wender and T.M. Dore Cyclization of Stilbene and its Derivatives, A. Gilbert Ene Reactions with Singlet Oxygen, A.G. Griesbeck Photooxygenation of 1,3-Dienes, W. Adam and A.G. Griesbeck Photorearrangement of Endope roxides, J. Rigaudy Photochemical Methods for the Synthesis of 1,2-Dioxetanes, A.L. Baumstark and A. Rodriguez Oxidation of Aromatics, A. Albinia and M. Freccero Cyclobutane Photochemistry, K. Mizuno and C. Pac Photochemistry of Oxiranes - Photoreactions of Epoxynaphthoquinones, K. Maruyama and Y. Kubo Photodecarboxylation of Acids and Lactones, P. Wan and D. Budac The Photochemistry of Esters of Carboxylic Acids, J.A. Pincock Carbene Formation in the Photochemistry of Cyclic Ketones, S.M. Roberts Norrish Type I Processes of Ketones: Basic Concepts, C. Bohne Norrish Type I Processes of Ketones: Selected Examples and Synthetic Applications, C. Bohne Photoinduced Intermolecular Hydrogen Abstraction Reactions of Ketones, M. Rubin Hydrogen Abstraction Reactions of a-Diketones, M. Rubin Norrish Type II Photoelimination of Ketones: Cleavage of 1,4-Biradicals Formed by y-Hydrogen Abstraction, .J.-P. Wagner Norrish

596 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
20231
20212
20203
20191
20183
20179