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Generation and Reactions of Organic Radical Cations in Zeolites
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Generation and Reactions of Organic Radical Cations in Zeolites Hermenegildo Garcı´a*,† and Heinz D. Roth*,‡,§ Departamento de Quı´mica/Instituto de Tecnologı´a Quı´mica UPV-CSIC, Universidad Polite´cnica de Valencia, Camino de Vera s/n, Apartado 22012, E-46071-Valencia, Spain, and Department of Chemistry and Chemical Biology, Rutgers University, Wright-Rieman Laboratories, New Brunswick, New Jersey 08854-8087 Contents I. Introduction 3948 II. Zeolites as Hosts 3949 II.A Chemical Composition, Crystal Structure, Characterization 3949 II.B Nature of the Active Sites 3951 II.B.1 Redox Reactivity and Acidity 3951 II.B.2 Influence of Oxygen 3952 II.C Characterization of Zeolite Active Sites Exemplified 3953 III. Adsorption Procedures 3954 IV. Experimental Techniques to Study Radical Cations in Zeolites 3955 IV.A Optical Absorption Spectroscopy 3955 IV.B IR and Raman Spectroscopy 3956 IV.C Magnetic Resonance Methods 3956 V. Spontaneous Generation of Radical Cations in Zeolites 3957 V.A Spontaneous Radical Cation Formation Exemplified 3957 V.A.1 Radical Cations from Alkenes 3957 V.A.2 Radical Cations from Alkynes 3959 V.A.3 Adsorption of Alkanes and Cycloalkanes 3959 V.A.4 Radical Cations from Cycloalkenes 3960 V.A.5 Adsorption of Benzene and Derivatives 3961 V.A.6 Radical Cations of R,ö-Diphenylpolyenes and Aryl Olefins 3963 V.A.7 Radical Cations of Polynuclear Aromatics 3964 V.A.8 Radical Cations of Nitrogen-Containing Substrates 3965 V.A.9 Radical Cations of Sulfur and Selenium-Containing Substrates 3967 V.A.10 Radical Cations of Organic Polymers Embedded in Zeolites 3970 V.A.11 Fullerene 3971 V.B Competition between Protonation and Oxidation 3971 V.B.1 Protonation vs Oxidation of Aromatic/ Unsaturated Hydrocarbons 3971 V.B.2 Protonation vs Oxidation of N,N¢-Diphenylhydrazine 3974 V.B.3 The Nature of the Blue Species Generated upon Adsorption of 1,1-Diarylethenes onto Acid Zeolites 3974 V.C Spontaneous Radical Cation Conversions in Zeolites 3976 V.C.1 Intra-Zeolite Reactions not Involving a Second Guest 3976 V.C.2 Ion-Ion or Ion-Molecule Reactions in Zeolites 3976 V.C.3 Spontaneous Deprotonation of Radical Cations 3977 VI. Generation of Radical Cations by Radiolysis in Zeolites 3978 VI.A Radical Cations of Linear and Branched Alkanes 3978 VI.B Radical Cations of Cycloalkanes 3979 VI.C Radical Cations of Strained Ring Substrates 3980 VI.D Radical Cations of Alkenes 3980 VI.E Radical Cations of C7H8-Isomers 3981 VI.F Radiolysis of Ethyne 3982 VI.G Radiolysis of Polynuclear Aromatics 3982 VII. Photochemical Generation of Radical Cations in Zeolites 3983 VII.A Zeolites as Inert Media: ET between Donor and Acceptor Guests 3983 VII.A.1 2,4,6-Triphenylpyrylium Ion as Electron Acceptor 3984 VII.A.2 Cyanoaromatics and Nitrogen Heterocycles as Acceptors 3986 VII.A.3 Acetophenone as Acceptor vs Aliphatic Amines 3986 VII.B Zeolites as Single Electron Acceptors: Photoionization inside Zeolites 3987 VII.B.1 Photochemistry of Aromatics in Zeolites 3987 VII.B.2 Photoionization of meso-Tetraphenylporphyrin 3988 VII.B.3 Photochemistry of Squaraines 3989 VII.B.4 Photochemistry of Aryl- and Diarylethylenes 3989 VII.B.5 Photochemistry of Bibenzyl Systems 3991 VII.B.6 Decarboxylation of Carboxylic Acids 3991 VII.C Viologens in Zeolites - Inert Media or Electron Acceptors 3991 VII.C.1 ET between Aromatic Donors and Viologen Acceptors 3991 VII.C.2 ET from Zeolites to Viologen Acceptors 3992 VII.C.3 Ruthenium Bipyridyl as Electron Donor 3993 VII.D Oxygen as Electron Acceptor: Visible Light Irradiation of Hydrocarbon ´ O2 CT Complexes inside Large-Pore Zeolites 3995 VIII. Electrochemical Generation of Radical Cations in Zeolites 3997 IX. Radical Anions within Zeolites 3998 X. Organic Radical Cations Generated in Inorganic Solids Related to Zeolites 4000 XI. Concluding Remarks and Perspective 4001 XII. Acknowledgments 4002 XIII. References 4002 [ Last edited by wxwdoctor on 2007-3-25 at 20:40 ] |
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