Photophysical and Photochemical Properties of Aromatic Compounds is the first book to collect and classify all available quantitative data on the photochemistry and luminescence of aromatic compounds. Compounds are classified by both spectral-luminescent (e.g., extinction coefficients, energies and lifetimes of lower excited states) and photochemical properties. In addition, all of the quantum yields available have been collected. The variety of photochemical reactions of aromatics is examined based on eight types of elementary monomolecular and bimolecular photochemical processes. Aromatic compounds are grouped into eight categories, and the book analyzes the possibilities of occurrence of all types of elementary photoprocesses.
INTRODUCTION. FUNDAMENTAL TENETS OF PHOTOCHEMISTRY AND PHOTOPHYSICS. PRINCIPLES OF CLASSIFICATION. MAIN DEFINITION. Photophysical Processes. Photochemical Processes. CLASSIFICATION OF MOLECULES BY SPECTRAL AND LUMINESCENT PROPERTIES. THEORETICAL IDEAS OF ELEMENTARY PHOTOCHEMICAL PROCESSES. Principles of Classification of Photochemical Processes. Photoionization and Electron Transfer. Proton Transfer. The Interrelation Between the Electron and Proton Transfer Processes. Hydrogen Atom Transfer. Pericyclic Reactions. Photosubstitution. Photodissociation. Photochemical Trans-Cis Isomerization. Valence Photoisomerization. SPECTRAL AND LUMINESCENT PROPERTIES OF AROMATIC HYDROCARBONS. UNSUBSTITUTED, ALKOXYSUBSTITUTED AND ALKYLSUBSTITUTED HYDROCARBONS. Electronic Structure. Individual Compounds of the Row of Unsubstituted Aromatic Hydrocarbons. AROMATIC COMPOUNDS OF THE CHAIN STRUCTURE. Polyphenyls. Diphenylpolyenes. Styrenes. Derivatives of Triphenylmethane and Triarylmethane Dyes. AROMATIC OXYCOMPOUNDS. Phenols. Naphthols. AROMATIC AMINES. Aniline. Aminonaphthalenes. Spectroscopic Properties in Ethanol. Dependence of Fluorescence Quantum Yield on Excitation Energy. Acid-Base Properties in the Ground and Excited States. The Luminescence Properties of Amine Molecules with a "Twisted Intramolecular Charge Transfer State" (TICT). Nitroanilines. HALOGENATED AROMATIC HYDROCARBONS. AROMATIC NITROCOMPOUNDS. PHOTOCHEMICAL PROPERTIES OF AROMATIC HYDROCARBONS. NONSUBSTITUTED, ALKYL- AND ALKOXYSUBSTITUTED COMPOUNDS. Valence Photoisomerization. Photodissociation. H-Abstraction. Photoionization and Electron Transfer. Pericyclic Reactions. Photosubstitution. HYDROCARBONS WITH CHAIN STRUCTURE. Cis-Trans Photoisomerization. Cyclization. Photodimerization. Photocycloaddition. Electron Transfer and Interactions with Charge Transfer. Proton Transfer. Bond Photodissociation in the ß-Position to Aromatic Ring. AROMATIC OXYCOMPOUNDS. Homolytic Photodissociation. Photoionization and Electron Transfer. Proton Transfer. Valence Isomerization. AROMATIC AMINES. Photodissociation of the N-H Bond. Dissociation of the C-N Bond. Cyclization. Photoionization. Electron Transfer. Photosubstitution. Triarylmethanes. NITRO COMPOUNDS. Electron and Hydrogen Atom Transfer. Photocycloaddition to NO2-Group. Nitro-Nitrit Rearrangement. Acid-Basic Dissociation. Photosubstitution. AROMATIC NITRILES. Benzonitrile. 1,4-Dicyanobenzene. 1,2,3,4-Tetracyclobenzene. 1- and 2-Cyanonaphthalenes. 1,4-Dicyanonaphthalene. Cyanoanthracene, -Phenanthrene and Higher Hydrocarbons. HALOGENAROMATIC COMPOUNDS. Valence Photoisomerization. Photodissociation. Electron Transfer in Fluorohydrocarbons. Photocycloaddition. Photosubstitution. REFERENCES. TABLES. FIGURE CAPTIONS. FIGURES. LIST OF ABBREVIATIONS. LIST OF SYMBOLS. APPENDIX. SUPPLEMENT. Notes to Tables. Luminescence Parameters of Aromatic Compounds Without Functional Substituents. Luminescence Parameters of Biphenyls, Terphenyls, and Fluorens. Luminescence Parameters and Quantum Yields of Monomolecular Rearrangement of the Stilbene Derivatives. Luminescence Parameters of Diphenylpolyenes and Styrenes. Luminescence Parameters and Quantum Yields of Photodissociation of Triarylmethanes. Luminescence Parameters of Aromatic Oxycompounds. Parameters for the Acid-Base Dissociation of the Aromatic Oxycompounds and Amines. Luminescence Parameters of Aromatic Amines. Luminescence Parameters of Nitrocompounds. Luminescence Parameters of Aromatic Nitriles. Photochemical Reactions of Nonsubstituted, Alkyl- and Alkoxysubstituted Aromatic Compounds. Quantum Yields of Cycloreversion and O-O-Rupture of Endoperoxides of Aromatic Compounds. Photoaddition of Olefins to Benzene. Biomolecular Photochemical Reactions of Diphenylpolyenes and Styrenes. Photochemical Reactions of Oxycompounds. Photochemical Reactions of Aromatic Amines. Photochemical Reactions of Nitrocompounds. Photochemical Reactions of Nitriles. Photochemical Reactions of Halogenaromatics.