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References

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Index

ab initio methods, 137, 165 Absorbance, 29 Absorptance, 30 Absorption, 27

coefÞcient. See molar absorption coefÞcient Absorption spectrum, 227, 275, 293, 340, 346,

381, 390 Acetaldehyde, 303 Acetamide, 361

Acetone, 58, 162, 224, 294, 321 enol, 218

Acetophenone, 251, 263, 294, 313, 325 2-methyl, 323

enol, 219

aci-nitro tautomer, 363 Acrylamide, 243 Acrylate

methyl ester, 352 Acrylonitrile, 426

Actinometry, 112, 113, 313, 416 Action spectrum, 88

Acyl radical, 305 Acyl shift, 247, 250

Adamantanethione, 381 Addition

nucleophilic, 252 Adhesive, 439 Adiabatic reaction, 68

Advanced oxidation process (AOP), 440 Aerosol particle, 361

Aggregate, 261, 308 AIBN, 434 Alcohol, 252 Aldehyde, 294

aliphatic, 302 Alkane, 391

Alkene, 227, 252, 255, 256, 300, 412, 420 aliphatic, 231, 238

aryl, 232, 252, 259 tethered, 262

Alkoxy radical, 298, 312 Alkyne, 227, 252, 256, 261 Allylic shift, 246

Alternant hydrocarbon (AH), 156 Amide, 452

Amine, 255 alkyl, 370

Amino acid, 265, 361 Aminobutyric acid, g-, 334

ester, 334 Aminolevulinic acid, 410 Anatase, 444

Aniline, 340

Anion-radical intermediate, 289 Anisole, 281, 285

Anisotropy degree, 93

Annealing, 443

Annulation, 271

Antarafacial approach, 246, 336 Anthracene, 43, 47, 71, 101, 135, 154, 164,

179, 186, 224, 286 Anthraquinone, 191, 295 Antiaromatic, 174, 203 Antibiotics, 409 Anti-Markovnikov addition, 253 Anti-Markovnikov product, 372 Anti-Stokes shift, 43 Antisymmetric function, 19, 150 Apoptosis, 411

Aqueous solution, 259 Aromatic

compound, 274, 287, 412, 416, 450

hydrocarbon, 37, 40, 64, 154, 185 nitrile, 371

Photochemistry of Organic Compounds: From Concepts to Practice Petr Klán and Jakob Wirz © 2009 P. Klán and J. Wirz. ISBN: 978-1-405-19088-6

550

Aromatic substitution radical, 399

Artemisinin, 420

ArtiÞcial photosynthesis, 430 Aryne, 335

Asymmetric synthesis, 238, 240, 254, 260 Atmosphere, 361, 406

Atomic units, 468 ATP, 364

ATP synthase, 428 Aufbau principle, 138 Auxochrome, 5, 229 Average chain length, 391 Avoided crossing, 69 Aza-di-p-methane, 251 Azalactam, 370

Azanaphthalene N-oxide, 359 Azide, 201, 355, 357

acyl, 356 aryl, 356 phenyl, 202

Azirine, 351, 426

Azo compound, 343, 351 cyclic, 344

Azoalkane, 210, 340, 344

Azobenzene, 117, 202, 340, 345, 349, 379 Azobisisobutyronitrile, 2,20 -, 351 Azodinorbornane, 344

Azomethane, 341

Azopyridine, 348 Azulene, 40, 156, 163, 179

Back electron transfer, 189 Bacteriochlorin, 341 Bacteriochlorophyll, 427 Bacteriopheophytin, 427 Barrelene, 248

Barton reaction, 343, 359 Basis set, 21

Beckmann-type photorearrangement, 350

Beer, 310

BeerÐLambert law, 29, 104 Benzaldehyde, 302, 324, 352 Benzene, 23, 276, 279, 285, 394

alkyl, 392 Benzenediazonium salt, 355 Benzene polycarboxylate, 238 Benzenoid hydrocarbon, 274 Benzhydrol, 299

Index

Benzophenone, 39, 58, 78, 127, 131, 162, 176, 212, 263, 295, 298, 299, 357, 426, 433

Benzoquinone, 327

Benzotriazole, 360

Benzoxazepine, 359

Benzoxazine, 434

Benzvalene, 276

Benzyl phenyl ketone, 305 Biacetyl, 58, 71, 89, 295, 298 Bicycle-pedal mechanism, 235 Bicyclo[2.1.0]pentane, 211 Bicyclo[2.2.2]octa-2,5,7-triene, 248

Bicyclo[2.2.2]octane, 2-benzoyl, 318 Bicyclo[2.2.2]octenone, 247 Bicyclo[3.1.0]hexanone, 271 Bicyclo[4.3.0]nona-2,4-diene, 242 Bilirubin, 237

Bioluminescence, 223, 224 Biomolecule, 357 Biphenyl

halogenated, 399 polychlorinated, 399

Biphenylyl tert-butyl ketone, 306 Biradical, 71, 125, 206, 248, 249, 255, 256,

267, 268, 271, 277, 300, 309, 311, 312, 317, 323, 328, 334, 352, 383, 388, 405,413, 420

conjugated, 206 cyclization, 312 deÞnition, 207 disjoint, 209 Kekule, 207, 210 localized, 206 nondisjoint, 209 non-Kekule, 207

Biradicaloid, 207 Bis(trißuoromethyl)thioketene, 381 Black-body radiator, 2, 31, 48 Bohr magneton, 16

Bond order, 143

Born interpretation, 18, 138, 148, 159 BornÐOppenheimer approximation, 14, 23, 35 Bromide

alkyl, 396 vinyl, 398 Bromine, 391

Bromophenol, 2-, 399, 400

Bromotrichloromethane, 397 But-2-ene, 257, 392 Butadiyne, 261

Index

Butyraldehyde, 330

Butyrophenone, a-methyl, 318

Ca2+ delivery, 364, 367 Cadmium sulÞde, 445

Cage compound, 264, 286, 401 Cage effect, 44, 308

Caged compound, 364 Camphorquinone, 439 Caprolactam, 394 Carbamate, 335

Carbene, 231, 352, 353, 354 Carbohydrate, 387

Carbon dioxide, 336 Carbon monoxide, 337 Carbonate, 335

Carbonyl compound, 293, 297, 300, 316 unsaturated, 268

Carboxylic acid, 331, 336 aryl ester, 335

ester, 332 Carotenoid, 427 Cascade reaction, 373 Catalysis, 257, 338 Cation

aryl, 289, 355 phenyl, 288, 402 vinyl, 397

Cationic polymerization, 402, 434 Cation-radical intermediate, 289

C-atom attack, Paterno`ÐB€uchi reaction, 302 Cavity

of reaction, 308 Chain reaction, 291, 435 Channel three, 41 Character table, 149 Charge

coupled device (CCD), 80 density, 143 recombination, 306 separation, 428, 431, 444 transfer, 257, 281

absorption, 281 complex, 191, 280 excited state, 185

intramolecular (ICT), 191

planar intramolecular (PICT), 191 state, 190

transition, 162

twisted intramolecular (TICT), 191

551

Chemiexcitation, 223 Chemiluminescence, 223, 414 Chiral

auxiliary, 316 crystal lattice, 315

space group, 239, 260 Chirality control, 238 Chlorin, 341

Chlorination selectivity, 391 Chlorine, 391

addition, 392 nitrate, 407

Chloroadamantane, 1-, 391 Chloroaniline, 4-, 288 Chlorobenzene, 289 Chloroßuorocarbon, 407 Chlorophyll, 341, 394 Cholecalciferol, 243 Chromatic orthogonality, 368 Chromene, 346 Chromophore, 5

Chrysene, 281 CIDNP, 204, 205 CIEEL, 224 Cinnamate

methyl ester, 281 Circularly polarized light, 238 Cis effect, 420

Cis-peak, 171

Citronellol, 395

Cleavage, a-, 305 Closed shell, 139 Coating, 439 Colour

additive, 11 complementary, 11 perception, 11 spectral, 11 subtractive, 12 triangle, 11

Colour photography, 448 Combinatorial synthesis, 366 Comet, 361

Compact disc, 348 Complexation, 349

Concerted mechanism, 248, 256, 412 Conduction band, 442

ConÞguration

closed shell, 139, 151 diagram, 166

552

ConÞguration (Continued) electronic, 139, 151 interaction (CI), 166 Confocal microscopy, 133

Conical intersection, 69 Conrotatory mode, 241

Constraining environment, 259, 308, 314 Copper(I) catalysis, 257, 258, 263 Correlation

diagram, 175 error, 138, 165 Co-sensitizer, 372 Cosmetics, 348, 364

Coulomb integral, 141

repulsion integral, 160 CoulsonÐRushbrooke pairing theorems, 156,

166 Crotononitrile, 281 Crown ether, 349 Crystal surface, 260 Crystals, organic, 260 Cubane, 264

Curtius-type rearrangement, 356 Cyanobacteria, 428 Cyanocobalamin, 379 Cycl[3.3.3]azine, 40, 156, 163

Cycloaddition, 262, 327, 352, 383, 412 Cycloalkane, 253, 433

Cycloalkene, 231, 252 Cycloaromatization, 300, 494 Cyclobut-a, 258 Cyclobutane, 257, 268, 328 Cyclobutanol, 323 Cyclobutene, 241 Cycloheptene, 232 Cyclohex-2-enone, 272, 372 Cyclohexa-2,5-dione, 272 Cyclohexanone oxime, 350 Cyclohexene, 253, 263 Cyclooctatetraene, 249 Cyclooctene, 232, 238, 240 Cyclopentanediol, 309 Cyclopentanone, 269, 269 Cyclopenten-2-one, 278 Cyclopentene, 231 Cyclophane, 262, 286 Cyclopropyl group, 284 Cycloreversion, 418 Cysteine, 310

Index

Cytochrome bc, 428

Cytochrome c, 427

Cytosine, 265

Cytotoxicity, 417

dÐd transition, 337 DDT, 399

de Mayo reaction, 271, 321 Death

of cell, 265, 411 Debye unit, 32

Decarbonylation, 305, 306, 308 Decarboxylation, 322 Degenerate, 19

wavefunctions, 142 Dehydroazepine, 356 Dehydrobenzene, 267 Dehydrocholesterol, 243, 244, 394 Dehydrohumulinic acid, 310 Dendrimer, 233

Density functional theory, 137, 171 Dental polymer, 439

Desilylation, 372

Detergent, 308 Dewar

benzene, 276 PMO theory, 156

Dexter mechanism, 57 Diabatic

reaction, 68, 69, 223 surfaces, 70

Diarylethene, 246 Diastereoselectivity, 248

Diazabicyclo[2.2.1]hept-2-ene, 344, 345 Diazabicyclo[2.2.2]oct-2-ene, 54, 341, 345 Diazacyclophane, 286

Diazirines, 3H, 352, 357 Diazo compound, 352, 357 Diazo-1,3-indandione, 353 Diazoalkane, 352

Diazocarbonyl compounds, -, 353 Diazomethane, 341, 353 Diazonaphthoquinone, 438 Diazonium salt, 287

aryl, 287 Dibenzo-p-dioxin, 399 Dibenzyl ketone, 308 Dichlorobutane, 2,3-, 392 Dicyanoanthracene, 9,10-, 372

Dicyanobenzene, 1,4-, 289, 372

Index

Dicyanoethylene, 302 Dicyanonaphthalene, 1,4-, 426 DielsÐAlder reaction, 285, 323 Diene, 328, 412, 419

Diene, 1,3-, 227

Dienophile, 323

Diepoxide, 418 Diethoxyethylene, 302 Diffusion-controlled reactions, 44

Dihydro-2,2,7,7-tetramethylpyrene, 346 Dihydrofuran, 302 Dihydronaphthodiazepine, 1,4-, 344 Dihydrophenanthrene, 232 Dihydropyridone, 304

Diketone, 321 1,2-, 271 1,3-, 271 a-, 298

Dimerization, 257 Dimethoxybenzoin group, 368 Dimethylaniline, 375 Dimethylhexatriene, 2,5-, 243 Dimethylpent-2-ene, 3,4-, 238 Dioxetane, 412, 413

Dioxole, 1,3-, 285 Dioxygen, see oxygen, 3 Diphenylcarbene, 354

Diphenylcyclohexanone, 2,6-, 309 Diphenyldiazomethane, 354 Diphenylethane, 1,1-, 372 Diphenyliodonium trißate, 402 Diphenylmethylene, 354 Diphenylvinylpropene, 249 Dipole moment, 20 Dipropylnaphthalene, 2,3-, 267 Diradical. See biradical Disproportionation, 306 Disrotatory mode, 241

Dissociation energy, 305, 337, 386, 391 of bond, 305

Dissolved organic material, 411 Di-tert-butyl ketone, 306 Di-p-methane rearrangement, 248

DNA, 53, 60, 191, 265, 266, 353, 357, 361, 378, 417 photochemical stability, 265

Doublet state, 17 DVD, 348 Dyad, 431 Dysidiolide, 416 ECL, 224

553

EDA complexes, 185 EfÞciency, 45, 52, 100, 119 Eigenfunction, 13, 22 Eigenvalue, 13, 22 Eigenvector, 22, 105 Einstein

coefÞcients, 30 equation, 9

Einstein unit, 110

El Sayed rules, 38, 172, 295 Electrochemical potential, 443 Electrocyclization, 232, 241, 246 Electron

acceptor, 371, 374 donor, 298, 374 hole, 442

spin. See spin

transfer, 121, 184, 188, 189, 191, 289, 321, 331, 355, 372, 379, 399, 401, 426, 431, 442

free energy of, 185 inner-sphere, 188 intramolecular, 189 outer-sphere, 188 return (RET), 184, 224

Electron transfer

photoinduced, 255, 256, 287, 317, 367 Electronic

conÞguration, 139 states, 15

transition moment, 34, 152 Electronics

molecular, 379 Elementary process, 99, 183 Elimination, Norrish

type II reaction, 215 Enamine, 414

Enantiodifferentiating photoisomerization, 240 Enantiodifferentiation, 239

Enantiomeric excess, 238, 316 Encounter complex, 45, 58 Endogenous photosensitizer, 410 Endoperoxide, 212, 404, 409, 412, 413 Ene reaction, 395, 414, 419

Energy gap law, 36, 40 Energy transfer, 47, 424

critical transfer distance, 50 Dexter mechanism, 57 exciton hopping, 54 F€orster-type resonance, 50 FRET, 50

554

Energy transfer (Continued) nonradiative, 49 nonvertical, 59 orientation factor, 51 radiative, 26 singletÐsinglet, 57

triplet sensitization, 57 tripletÐsinglet, 55 tripletÐtriplet, 57, 64 trivial, 48

Enol, 218, 252, 271 Enolate, 290 Enone, 250, 257

cyclic, 272

cyclic, type A reaction, 271 cyclic, type B reaction, 271 b,g-, 250

Environmental chemistry, 400 Enzyme activity, 364

Eosin, 63 Ergocalciferol, 243 Ergosterol, 394 Erythrolide A, 249 Ester

unsaturated, 234 Etching, 437 Ethyl acetate, 332

Ethynylbenzene, 281

E-type delayed ßuorescence, 63 Evolving factor analysis, 108 Exchange integral, 160, 209 Excimer, 60

Exciplex, 63, 125, 184, 255, 256, 268, 281, 300, 328, 399, 420

Excitation energy, 298, 305, 383, 396 Exciton, 427, 442, 445

interaction of, 62 Expectation value, 21 Eyeglass, 346

EÐZ isomerization, 375

EÐZ photoisomerization, 228, 229, 242, 253, 325, 343, 349, 375, 394, 379

Factor analysis, 103, 105 Falling-Þlm reactors, 83 Fatigue, photochromism, 346 FentonÕs reagent, 440

Fermi

golden rule, 36, 50, 172, 190 hole, 20, 140, 160

Index

Ferredoxin, 428 Ferric ion, 440 Ferrioxalate ion, 441 Filter

cut-off, 73, 97 cut-on, 73 dichroic, 79

inner Þlter effect, 87 Fluorescein, 43, 64 Fluorescence, 28, 87, 275

conversion to wavenumber, 90 correction of spectra, 90 correlation analysis, 134 delayed, 40, 63 depolarization, 49

dual, 190

E-type delayed, 63 excitation spectra, 88 lifetime, 91, 121 prompt, 63

P-type delayed, 63 quenching, 302

Fluoroacetophenone, 400 Forbidden transitions, 34 F€orster, 5

critical transfer distance, 55 cycle, 193

Fragmentation, 268 FranckÐCondon

integral, 34, 36, 41 principle, 41, 43, 67, 174, 41

Fraunhofer lines, 2 FreezeÐpumpÐthaw method, 83 Freon, 407

Frequency combs, 78 Freshwater, 411 FRET, 50

FriedelÐCrafts acylation, photochemical, 330 Frozen core approximation, 140

Fulgide, 346 Fullerene, 282, 432 Fulvene, 276 Funnel, 69

GABA, 334

GFP, 134

Glucuronidation, 237

Gr€atzel cell, 446

Green photochemistry, 330

Green plant, 428

 

 

Index

 

 

 

 

 

 

555

Grob fragmentation, 268, 312

molecular orbital (HMO), 140

Ground-state conformational control of

operator,

144

 

 

photoreactivity, 235

Hue, 12

 

 

 

 

 

 

Group theory,

148

Hula twist,

235

 

 

Guanine, 378

 

Humic acid, 411

 

 

Guanosine, 417

HundÕs rule,

20, 65, 140, 151, 205,

 

 

 

207

 

 

 

 

 

Haematoporphyrin, 410

Hybridization,

293

 

Halide

 

 

Hydrocarbon

 

 

 

alkyl, 396

 

 

unsaturated,

227, 392,

aromatic,

287, 288, 398, 399

Hydrogen

 

 

 

 

 

Halogen

 

 

abstraction,

298, 300, 306, 311, 316, 323,

compounds,

390

327, 329, 359, 362, 383, 392, 396

molecule,

390

b-,

317

 

 

 

Halophenol,

400

d-,

319

 

 

 

 

Hamigerans,

324

e-, 320

 

 

 

 

Hamiltonian operator, 13

g-,

317

 

 

 

 

Hardening, 395

peroxide,

 

440

 

 

HartreeÐFock,

161

production,

374, 430

limit, 165

 

 

Hydroquinone,

367, 448

Head-to-head product, 269

Hydroxyl radical,

407, 450

Head-to-tail product, 269

4-Hydroxyphenacyl,

334

Heavy-atom effect, 173, 215, 233,

Hyperbilirubinaemia,

237

275, 398

Hyperconjugation,

159

Heisenberg uncertainty principle, 27, 77,

HyperÞne coupling, 38, 172

78, 109

 

Hypervalent iodine compound,

Helicene, 239, 245

402, 434

 

 

Haematite, 445

Hypobromite, 402

 

Haem oxygenase, 237

Hypochlorite, 403

 

 

Haemoglobin, 379

Hypohalite, 402

 

 

Heptadiene,

270

Hypoiodite,

 

402

 

 

Heterocyclic compound, 281

 

 

 

 

 

 

 

Heterogeneous photocatalysis, 119

Ice, 412, 361

 

 

 

Hexachlorobenzene, 401

Image intensiÞer,

8, 80

Hexachlorocyclohexane, 394

Imine, 343, 349

 

 

Hexad, 432

 

 

unsaturated,

251

 

Hexaßuorobenzene, 281

Improper rotation,

148

Hexamethylenetetramine, 361

Inclusion crystal, 239

Hexylamine,

291

Indole, 340

 

 

 

 

 

High-energy radiation, 361

Initiator

 

 

 

 

 

 

Holography,

261

radical reaction,

351

HOMOÐLUMO transition, 275

Ink, 439

 

 

 

 

 

 

Homoskedastic, 126

In-plane inversion, 343

Hopping mechanism, 192

Insecticide,

 

394

 

 

Hot bands, 35, 42

Integrated circuit,

353

Hot ground state reaction, 131

Intensity, 49

 

 

 

Hot-band mechanism, 59

Intercalator,

 

378

 

 

H€uckel

 

 

Interference,

11

 

 

aromaticity rule, 143

Internal conversion (IC), 27, 48

determinant,

141

Interstellar space,

361

556

Intersystem crossing, 27, 172, 256, 275, 298, 312, 385, 398,

oxygen-catalysed, 65 Intramolecular cyclization, 255 Iodide

alkyl, 396 vinyl, 397

Iodobenzene, 290, 402, Iodobiphenyl, 402 Iodocubane, 401

Ion pair contact, 184

solvent separated, 184 Ionic liquid, 299

Ionization potential, 299, 397 Iron pentacarbonyl, 442 Irreducible representation, 149 ISC

oxygen-catalysed, 212 Isocyanate, 356 Isohumulone, 310 Isooxyskytanthine, 322 Isosbestic point, 104, 114 Isotope effect, 37, 384

kinetic, 196 primary, 197 secondary, 197

Jabłonski diagram, 25

Kasha rule, 39, 40, 275, 382 Ketene, 400

a-Ketocarbene, 400 Ketone, 294, 305

2-alkylphenyl, 323 aliphatic, 298, 302, 312 alkyl, 312

aromatic, 298, 306, 312, 317 cyclic, 306

unsaturated, 336 b-alkoxy, 319

Ketoprofen, 331 Ketyl radical, 219 Kinetic clock, 284

Kinetic isotope effect, 420 KoopmansÕ theorem, 156, 161 Kronecker delta, 22, 103

Lactic acid, 450

Lactone, 334

Index

LandauÐZener model, 70, 223 Large-ring compound, 320 LASER, 31, 76, 77

continuous wave, 77 mode-locked, 77 Q-switched, 77

Laser printer, 448 Latent image, 437, 448 LCAO, 21

Least-motion pathway, 255, 260, 309 Leaving group, 365

LED, 375

Lewis acid catalysis, 234 Lifetime, 29, 121

ßuorescence, 91 radiative, 121

Ligand-to-ligand charge transfer, 337 Ligand-to-metal charge transfer, 337 Light-driven shuttle, 376 Light-harvesting antenna, 427, 431 Limonene, 254

Lindane, 394 Linker

photolabile, 366 Liposome, 367 Lithography, 353

Longer distance intramolecular hydrogen abstraction, 320

Lumiketone, 271

Luminescence, 29

conversion to wavenumber, 90 correction of spectra, 90

Lumirubin, 237 Lumisantonin, 272 Lyman-a emission, 361

Machine molecular, 375

Marcus inverted region, 187, 189, 428 Markovnikov addition, 252, 253, 254 Matrix, 103

diagonal, 103 identity, 103 inverse, 103 isolation, 130

photochemistry, 351, 352 singular, 103

square, 22, 103 symmetrical, 103 transpose, 103

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