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Journal articles on the topic 'Photochemistry; Benzophenones'

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Published: 4 June 2021

Last updated: 5 February 2022

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1

Ito, Yoshikatsu, Teruo Matsuura, Kenichi Tabata, Meng Ji-Ben, Keiichi Fukuyama, Masanori Sasaki, and Shuji Okada. "Solid state photochemistry of methyl-substituted benzophenones." Tetrahedron 43, no. 7 (January 1987): 1307–12. http://dx.doi.org/10.1016/s0040-4020(01)90251-0.

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2

WOODWARD, JONATHAN R., TIEN-SUNG LIN, YOSHIO SAKAGUCHI, and HISAHARU HAYASHI. "Biphotonic photochemistry of benzophenones in dimethylsulphoxide: a flash photolysis EPR study." Molecular Physics 100, no. 8 (April 20, 2002): 1235–44. http://dx.doi.org/10.1080/00268970110113551.

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3

Alten, Norman S., Michele Edge, Fernando Catalina, Teresa Corrales, Maria Blanco-Pina, and Arthur Green. "Photochemistry and photocuring activities of novel substituted 4′-(4-methylphenylthio) benzophenones as photoinitiators." Journal of Photochemistry and Photobiology A: Chemistry 110, no. 2 (October 1997): 183–90. http://dx.doi.org/10.1016/s1010-6030(97)00175-5.

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4

Basarić, Nikola, Devin Mitchell, and Peter Wan. "Substituent effects in the intramolecular photoredox reactions of benzophenones in aqueous solution." Canadian Journal of Chemistry 85, no. 9 (September 1, 2007): 561–71. http://dx.doi.org/10.1139/v07-081.

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A number of α-hydroxy-3-benzylbenzophenones 7–11 have been synthesized for the purpose of studying the effect of a phenyl substituent on the intramolecular photoredox reaction of 3-(hydroxymethyl)benzophenone (5) discovered in our laboratory. This latter compound was found to undergo a unimolecular (formal) intramolecular redox reaction upon photolysis in aqueous acid that results in clean reduction of the benzophenone ketone (to secondary alcohol) and oxidation of the alcohol to aldehyde. Three of the phenyl-substituted compounds with simple phenyl (7), p-methylphenyl (8), and p-methoxyphenyl (9) were found to undergo the acid-catalyzed intramolecular photoredox reaction with the observation that 9 also undergoes a residual photoredox reaction that is not acid-mediated and may involve initial photoinduced electron transfer, which is supported by LFP data. The m-methoxyphenyl (10) compound did not undergo the reaction. The trend in observed relative reactivity may be partially rationalized by examining changes in molecular orbital coefficients observed in the calculated HOMOs and LUMOs. The photoredox reaction has also been applied twice in succession in a single compound 11, demonstrating that the photoredox reaction may be useful for sequential photoredox reactions in a multifunctional compound.Key words: intramolecular photoredox, acid catalysis, meta effect, benzophenone photochemistry.

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5

Spighi, Gloria, Marc-André Gaveau, Jean-Michel Mestdagh, Lionel Poisson, and Benoît Soep. "Gas phase dynamics of triplet formation in benzophenone." Phys. Chem. Chem. Phys. 16, no. 20 (2014): 9610–18. http://dx.doi.org/10.1039/c4cp00423j.

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6

Liu, Wenying, Yishi Dong, Shuxiang Zhang, Zhaoqiang Wu, and Hong Chen. "A rapid one-step surface functionalization of polyvinyl chloride by combining click sulfur(vi)-fluoride exchange with benzophenone photochemistry." Chemical Communications 55, no. 6 (2019): 858–61. http://dx.doi.org/10.1039/c8cc08109c.

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7

Zhang, Shuxiang, Wenying Liu, Zhaoqiang Wu, and Hong Chen. "Tri-functional platform for the facile construction of dual-functional surfaces via a one-pot strategy." Journal of Materials Chemistry B 8, no. 26 (2020): 5602–5. http://dx.doi.org/10.1039/d0tb01222j.

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We designed a novel tri-functional platform and facilely constructed dual-functional surfaces in one pot by combining the “sulfur(vi)-fluoride exchange” (SuFEx) click reaction, photoinitiated polymerization and benzophenone photochemistry.

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8

Vieira Ferreira, L. F., A. I. Costa, I. Ferreira Machado, T. J. F. Branco, S. Boufi, M. Rei-Vilar, and A. M. Botelho do Rego. "Surface Photochemistry: Benzophenone as a Probe for the Study of Modified Cellulose Fibres." Research Letters in Physical Chemistry 2007 (January 17, 2007): 1–5. http://dx.doi.org/10.1155/2007/18278.

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This work reports the use of benzophenone, a very well characterized probe, to study new hosts (i.e., modified celluloses grafted with alkyl chains bearing 12 carbon atoms) by surface esterification. Laser-induced room temperature luminescence of air-equilibrated or argon-purged solid powdered samples of benzophenone adsorbed onto the two modified celluloses, which will be named C12-1500 and C12-1700, revealed the existence of a vibrationally structured phosphorescence emission of benzophenone in the case where ethanol was used for sample preparation, while a nonstructured emission of benzophenone exists when water was used instead of ethanol. The decay times of the benzophenone emission vary greatly with the solvent used for sample preparation and do not change with the alkylation degree in the range of 1500–1700 micromoles of alkyl chains per gram of cellulose. When water was used as a solvent for sample preparation, the shortest lifetime for the benzophenone emission was observed; this result is similar to the case of benzophenone adsorbed onto the “normal” microcrystalline cellulose surface, with this latter case previously reported by Vieira Ferreira et al. in 1995. This is due to the more efficient hydrogen abstraction reaction from the glycoside rings of cellulose when compared with hydrogen abstraction from the alkyl chains of the modified celluloses. Triplet-triplet transient absorption of benzophenone was obtained in both cases and is the predominant absorption immediately after laser pulse, while benzophenone ketyl radical formation occurs in a microsecond time scale both for normal and modified celluloses.

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9

Monti, Sandra, Lucia Flamigni, Alessandro Martelli, and Pietro Bortolus. "Photochemistry of benzophenone-cyclodextrin inclusion complexes." Journal of Physical Chemistry 92, no. 15 (July 1988): 4447–51. http://dx.doi.org/10.1021/j100326a040.

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10

Berger, Karen L., Alexandra L. Nemecek, and Christopher J. Abelt. "Photochemistry of benzophenone-capped .beta.-cyclodextrin." Journal of Organic Chemistry 56, no. 11 (May 1991): 3514–20. http://dx.doi.org/10.1021/jo00011a014.

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11

Belsom, Adam, Gemma Mudd, Sven Giese, Manfred Auer, and Juri Rappsilber. "Complementary Benzophenone Cross-Linking/Mass Spectrometry Photochemistry." Analytical Chemistry 89, no. 10 (May 4, 2017): 5319–24. http://dx.doi.org/10.1021/acs.analchem.6b04938.

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12

Da Silva, J. P., I. Ferreira Machado, J. P. Lourenço, and L. F. Vieira Ferreira. "Photochemistry of benzophenone adsorbed on MCM-41 surface." Microporous and Mesoporous Materials 84, no. 1-3 (September 2005): 1–10. http://dx.doi.org/10.1016/j.micromeso.2005.05.012.

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13

Da Silva, J. P., I. Ferreira Machado, J. P. Lourenço, and L. F. Vieira Ferreira. "Photochemistry of benzophenone on Ti-MCM-41 surfaces." Microporous and Mesoporous Materials 89, no. 1-3 (February 2006): 143–49. http://dx.doi.org/10.1016/j.micromeso.2005.10.011.

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14

Liu, Shaohui, Hong Chen, Yijun Zhang, Ke Sun, Yangyang Xu, Fabrice Morlet-Savary, Bernadette Graff, et al. "Monocomponent Photoinitiators based on Benzophenone-Carbazole Structure for LED Photoinitiating Systems and Application on 3D Printing." Polymers 12, no. 6 (June 22, 2020): 1394. http://dx.doi.org/10.3390/polym12061394.

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In this article, different substituents (benzoyl, acetyl, styryl) are introduced onto the carbazole scaffold to obtain 8 novel carbazole derivatives. Interestingly, a benzoyl substituent, connected to a carbazole group, could form a benzophenone moiety, which composes a monocomponent Type II benzophenone-carbazole photoinitiator (PI). The synergetic effect of the benzophenone moiety and the amine in the carbazole moiety is expected to produce high performance photoinitiating systems (PISs) for the free radical photopolymerization (FRP). For different substituents, clear effects on the light absorption properties are demonstrated using UV-Visible absorption spectroscopy. Benzophenone-carbazole PIs can initiate the FRP of acrylates alone (monocomponent Type II photoinitiator behavior). In addition, fast polymerization rates and high function conversions of acrylate are observed when an amine and/or an iodonium salt are added in systems. Benzophenone-carbazole PIs have good efficiencies in cationic photopolymerization (CP) upon LED @ 365 nm irradiation in the presence of iodonium salt. In contrast, other PIs without synergetic effect demonstrate unsatisfied photopolymerization profiles in the same conditions. The best PIS identified for the free radical photopolymerization were used in three-dimensional (3D) printing. Steady state photolysis and fluorescence quenching experiments were carried out to investigate the reactivity and the photochemistry and photophysical properties of PIs. The free radicals, generated from the studied PISs, are detected by the electron spin resonance - spin trapping technique. The proposed chemical mechanisms are provided and the structure/reactivity/efficiency relationships are also discussed. All the results showed that the benzophenone-carbazole PIs have a good application potential, and this work provides a rational design route for PI molecules. Remarkably, BPC2-BPC4, C6, C8 were never synthetized before; therefore, 5 of the 8 compounds are completely new.

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15

Buono-Core, G. E., A. H. Klahn, F. Aros, and V. Astorga. "Benzophenone sensitized photochemistry of a copper(II) polypyrazolylborate complex." Polyhedron 15, no. 2 (January 1996): 363–66. http://dx.doi.org/10.1016/0277-5387(95)00270-3.

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16

Wagner, Peter J., Brij P. Giri, Raul Pabon, and Surendra B. Singh. "Divergent photochemistry of 2,4-di-tert-butylacetophenone and -benzophenone." Journal of the American Chemical Society 109, no. 26 (December 1987): 8104–5. http://dx.doi.org/10.1021/ja00260a036.

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17

Allen, N. S., S. J. Hardy, A. F. Jacobine, D. M. Glaser, B. Yang, D. Wolf, F. Catalina, S. Navaratnam, and B. J. Parsons. "Photochemistry and photopolymerization activity of perester derivatives of benzophenone." Journal of Applied Polymer Science 42, no. 5 (March 5, 1991): 1169–78. http://dx.doi.org/10.1002/app.1991.070420501.

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18

Markovic, Dejan. "Photochemistry of aromatic ketones in sodium dodecyl sulphate micelles in the presence of unsaturated fatty acids." Journal of the Serbian Chemical Society 69, no. 2 (2004): 107–15. http://dx.doi.org/10.2298/jsc0402107m.

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Laser-flash photolysis has been employed to characterize the behaviour of the free radicals created in the photochemical reaction of benzophenone (BZP), as well as of its lipoidal derivative, benzophenone-4-heptyl-4?-pentanoic acid (BHPA), with chosen unsaturated fatty acids in sodium dodecyl sulphate micelles. The calculated rate constants were used to study the "cage effect" i.e., the recombination of the created radical-pairs (BZP, BHPA ketyl radical - lipid radical) inside the highly limited space of the SDS micelles. The "cage effect" appears to be the dominant event inside SDS micelles, dependent on the structure of both the reactants-precursors. The fractions of the initially created radical-pairs which escape the "cage effect" and exit into the surrounding aqueous phase do not exceed 16 %. This fact is of enormous importance for the self-control of the pathogenic process of lipid peroxidation.

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19

Lathioor, Edward C., and William J. Leigh. "Geometric and solvent effects on intramolecular phenolic hydrogen abstraction by carbonyl n,π* and π,π* triplets." Canadian Journal of Chemistry 79, no. 12 (December 1, 2001): 1851–63. http://dx.doi.org/10.1139/v01-167.

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The photochemistry of a series of alkoxyacetophenone, -benzophenone, and -indanone derivatives, which contain a remote phenolic group linked to the ketone by a para,para'- or meta,meta'-oxyethyl spacer, has been studied in acetonitrile and dichloromethane solutions using laser flash photolysis techniques. The corresponding methoxy-substituted compounds and, in the case of the alkoxyindanones, derivatives bearing just a remote phenyl substituent, have also been examined. The triplet lifetimes of the phenolic compounds are determined by the rates of intramolecular abstraction of the remote phenolic hydrogen, and depend on the solvent, the geometry of attachment and the configuration of the lowest triplet state. In contrast to the large (>500-fold) difference in lifetime of the para,para'- and meta,meta'-alkoxyacetophenone derivatives, both of which have lowest π,π* triplet states, smaller differences are observed for the alkoxyindanone (lowest charge transfer triplet, ~twofold difference) and alkoxybenzophenone (lowest n,π* triplet, ~18-fold difference) derivatives in acetonitrile solution. The triplet lifetimes of the acetophenone and benzophenone are significantly shorter in dichloromethane than in acetonitrile, consistent with the intermediacy of a hydrogen-bonded triplet exciplex in the reaction. This is not the case with the para,para'-indanone derivative, sugesting that hydrogen abstraction in this compound is dominated by a mechanism involving initial charge transfer rather than hydrogen bonding. This is most likely due to orientational constraints that prevent the remote phenolic -O-H group from adopting a coplanar arrangement with the n-orbitals of the carbonyl group.Key words: photochemistry, aromatic ketone, phenol, triplet, intramolecular, quenching, hydrogen abstraction, phenoxyl radical, kinetics, kinetic isotope effect, laser flash photolysis.

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20

Oatis, John E., and Daniel R. Knapp. "Synthesis and photochemistry of two cleavable heterobifunctional benzophenone protein crosslinkers." Tetrahedron Letters 39, no. 13 (March 1998): 1665–68. http://dx.doi.org/10.1016/s0040-4039(98)00016-1.

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21

Gao, Fang, Jianchao Wang, XiaoJiao Liu, Long Yang, Nvdan Hu, Ting Xie, Hongru Li, and Shengtao Zhang. "Synthesis, Spectroscopy and Photochemistry of Nitro-Azobenzene Dyes Bearing Benzophenone Parts." Journal of Fluorescence 19, no. 3 (November 19, 2008): 533–44. http://dx.doi.org/10.1007/s10895-008-0442-y.

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22

Vieira Ferreira, L. F., A. I. Costa, I. Ferreira Machado, and J. P. Da Silva. "Surface photochemistry: Benzophenone within nanochannels of H+ and Na+ ZSM-5 zeolites." Microporous and Mesoporous Materials 119, no. 1-3 (March 2009): 82–90. http://dx.doi.org/10.1016/j.micromeso.2008.09.041.

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23

Venkatraman, Ravi Kumar, and Andrew J. Orr-Ewing. "Photochemistry of Benzophenone in Solution: A Tale of Two Different Solvent Environments." Journal of the American Chemical Society 141, no. 38 (September 3, 2019): 15222–29. http://dx.doi.org/10.1021/jacs.9b07047.

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24

Shizuka, H. "Photophysics and photochemistry of triplet exciplexes between triplet naphthalene derivatives and benzophenone." Pure and Applied Chemistry 69, no. 4 (January 1, 1997): 825–30. http://dx.doi.org/10.1351/pac199769040825.

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25

Scaiano, J. C., A. F. Becknell, and R. D. Small. "Photochemistry of a benzophenone-containing bisimide: a model for inherently photosensitive polyimides." Journal of Photochemistry and Photobiology A: Chemistry 44, no. 1 (July 1988): 99–110. http://dx.doi.org/10.1016/1010-6030(88)85009-3.

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26

Casal, H. L., and J. C. Scaiano. "Intrazeolite photochemistry. II. Evidence for site inhomogeneity from studies of aromatic ketone phosphorescence." Canadian Journal of Chemistry 63, no. 6 (June 1, 1985): 1308–14. http://dx.doi.org/10.1139/v85-222.

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The luminescent properties of several aromatic ketones included in the hydrophobic zeolite Silicalite have been examined. Acetophenone, benzophenone, and β-phenylpropiophenone show readily detectable phosphorescence; by contrast, valerophenone does not luminesce, but undergoes the Norrish Type II reaction. Thus, irradiated samples of valerophenone in Silicalite show phosphorescence due to the accumulation of acetophenone. In the case of β-phenylpropiophenone the triplet lifetime is ca. 100 000 times longer than the solution value, suggesting severe conformational restrictions. Co-inclusion of acetophenone with various substrates and oxygen quenching studies indicate that Silicalite has at least two distinct classes of inclusion sites. In one of them energy transfer processes are rapid and efficient, suggesting a cooperative effect in the inclusion of ketones in these regions of the Silicalite framework.

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27

Buono-Core, G. E., and G. Leon R. "Benzophenone sensitized photochemistry of Cu(II) and Ni(H) complexes with 4-acylpyrazolones." Inorganica Chimica Acta 159, no. 2 (May 1989): 133–35. http://dx.doi.org/10.1016/s0020-1693(00)80554-x.

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28

Allen, N. S., F. Catalina, J. L. Mateo, R. Sastre, P. N. Green, and W. A. Green. "Photochemistry of novel water-soluble parasubstituted benzophenone photoinitiators: A photocalorimetric and photoreduction study." Journal of Photochemistry and Photobiology A: Chemistry 44, no. 2 (August 1988): 171–77. http://dx.doi.org/10.1016/1010-6030(88)80089-3.

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29

Churio, M. S., and M. A. Grela. "Photochemistry of Benzophenone in 2-Propanol: An Easy Experiment for Undergraduate Physical Chemistry Courses." Journal of Chemical Education 74, no. 4 (April 1997): 436. http://dx.doi.org/10.1021/ed074p436.

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30

SHIZUKA, H. "ChemInform Abstract: Photophysics and Photochemistry of Triplet Exciplexes Between Triplet Naphthalene Derivatives and Benzophenone." ChemInform 28, no. 44 (August 3, 2010): no. http://dx.doi.org/10.1002/chin.199744326.

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31

Horie, Kazuyuki, Masako Tsukamoto, Keiko Morishita, and Itaru Mita. "Photochemistry in Polymer Solids V. Decay of Benzophenone Phosphorescence in Polystyrene and in Polycarbonate." Polymer Journal 17, no. 3 (March 1985): 517–24. http://dx.doi.org/10.1295/polymj.17.517.

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32

Horie, Kazuyuki, Harumi Ando, and Itaru Mita. "Photochemistry in polymer solids. 8. Mechanism of photoreaction of benzophenone in poly(vinyl alcohol)." Macromolecules 20, no. 1 (January 1987): 54–58. http://dx.doi.org/10.1021/ma00167a011.

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33

Chen, Xuebo, Qiangqiang Zhang, Yanchang Xu, Weihai Fang, and David Lee Phillips. "Water-Assisted Self-Photoredox of 3-(Hydroxymethyl)benzophenone: An Unusual Photochemistry Reaction in Aqueous Solution." Journal of Organic Chemistry 78, no. 11 (May 21, 2013): 5677–84. http://dx.doi.org/10.1021/jo4008783.

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34

Costela, A., J. Dabrio, J. M. Figuera, I. García-Moreno, H. Gsponer, and R. Sastre. "Photochemistry of the photoinitiator 4-[2′-N-N,-(diethylaminoeethoxy]-benzophenone. Spectroscopy, radical generation and quenching." Journal of Photochemistry and Photobiology A: Chemistry 92, no. 3 (December 1995): 213–21. http://dx.doi.org/10.1016/1010-6030(95)04135-9.

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35

Adam, Waldemar, and Ralf Finzel. "UV-laser photochemistry: Retro-cleavage in the benzophenone-sensitized photolysls of Δ3-1,3,4-Oxadiazolines into diazoalkanes." Tetrahedron Letters 31, no. 6 (January 1990): 863–66. http://dx.doi.org/10.1016/s0040-4039(00)94648-3.

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36

Ferreira, L. F. Vieira, I. Ferreira Machado, J. P. Da Silva, and T. J. F. Branco. "Surface photochemistry: benzophenone as a probe for the study of silica and reversed-phase silica surfaces." Photochemical & Photobiological Sciences 5, no. 7 (2006): 665. http://dx.doi.org/10.1039/b600384b.

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37

Allen, Norman S., Edward Lam, Edward M. Howells, Peter N. Green, Arthur Green, Fernando Catalina, and Carmen Peinado. "Photochemistry and photopolymerization activity of novel 4-alkylamino benzophenone initiators-synthesis, characterization, spectroscopic and photopolymerization activity." European Polymer Journal 26, no. 12 (January 1990): 1345–53. http://dx.doi.org/10.1016/0014-3057(90)90149-x.

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38

Allen, N. S., W. Chen, F. Catalina, P. N. Green, and A. Green. "Photochemistry of novel water-soluble para-substituted benzophenone photoinitiators: A polymerization, spectroscopic and flash photolysis study." Journal of Photochemistry and Photobiology A: Chemistry 44, no. 3 (September 1988): 349–60. http://dx.doi.org/10.1016/1010-6030(88)80105-9.

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39

Allen, N. S., E. Lam, J. L. Kotecha, W. A. Green, A. Timms, S. Navaratnam, and B. J. Parsons. "Photochemistry of novel 4-alkylamino benzophenone initiators: a conventional laser flash photolysis and mass spectrometry study." Journal of Photochemistry and Photobiology A: Chemistry 54, no. 3 (November 1990): 367–88. http://dx.doi.org/10.1016/1010-6030(90)85009-l.

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40

Nakatani, Kazuhiko, Takashi Yoshida, and Isao Saito. "Photochemistry of Benzophenone Immobilized in a Major Groove of DNA: Formation of Thermally Reversible Interstrand Cross-link." Journal of the American Chemical Society 124, no. 10 (March 2002): 2118–19. http://dx.doi.org/10.1021/ja017611r.

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41

Hoshino, Mikio, and Haruo Shizuka. "Photochemistry of benzophenone in aliphatic amines studied by laser photolysis in the temperature range 300-77 K." Journal of Physical Chemistry 91, no. 3 (January 1987): 714–18. http://dx.doi.org/10.1021/j100287a044.

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42

Pacut, Ryszard, Michelle L. Grimm, George A. Kraus, and James M. Tanko. "Photochemistry in supercritical carbon dioxide. The benzophenone-mediated addition of aldehydes to α,β-unsaturated carbonyl compounds." Tetrahedron Letters 42, no. 8 (February 2001): 1415–18. http://dx.doi.org/10.1016/s0040-4039(00)02273-5.

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43

Nakagaki, Ryoichi, Masaharu Yamaoka, Osamu Takahira, Ken-ichi Hiruta, Yoshihisa Fujiwara, and Yoshifumi Tanimoto. "Magnetic Field and Isotope Effects on Photochemistry of Chain-Linked Compounds Containing Benzophenone and Hydrogen-Donor Moieties." Journal of Physical Chemistry A 101, no. 4 (January 1997): 556–60. http://dx.doi.org/10.1021/jp961893d.

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44

Martínez, L. J., and J. C. Scaiano. "Transient Intermediates in the Laser Flash Photolysis of Ketoprofen in Aqueous Solutions: Unusual Photochemistry for the Benzophenone Chromophore." Journal of the American Chemical Society 119, no. 45 (November 1997): 11066–70. http://dx.doi.org/10.1021/ja970818t.

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45

Kell, Arnold J., Christopher C. Montcalm, and Mark S. Workentin. "Photogeneration of a diene template for surface DielsAlder reactions: Photoenolization of an ortho-methyl-benzophenone-modified Au cluster." Canadian Journal of Chemistry 81, no. 6 (June 1, 2003): 484–94. http://dx.doi.org/10.1139/v03-031.

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A series of monolayer-protected clusters (MPCs) modified with a photoreactive [4-(11-mercaptoundecyl)-phenyl](2-methylphenyl)methanone (1) moiety have been prepared where 1 is co-absorbed to the MPC surface with dodecanethiol, octadecanethiol, or 11-mercaptoundecanoic acid methyl ester. Upon irradiation the MPC-anchored 1 reacts efficiently through its triplet excited states, yielding 1,4-biradicals that collapse to synthetically useful, long-lived photodienol intermediates, which can be efficiently trapped in DielsAlder type chemistry by dienophiles namely, dimethyl acetylenedicarboxylate (DMAD). In all cases the DielsAlder trapping of the dienol occurred efficiently resulting in >60% conversion to the DielsAlder adduct. This indicates that the local environment surrounding 1 did not influence its ability to react via the DielsAlder reaction; however, the reaction could not be taken to completion. The inability to react completely is attributed to 1 binding to distinct sites on the MPC core; there are edge, vertice, and terrace sites. Selective population of these specific sites and the subsequent irradiations show that MPCs with 1 anchored predominantly at edge and vertice sites results in an extent of reaction of 85 ± 3%, whereas selectively populating the terrace sites results in an extent of reaction of 36 ± 2%. These results suggest that 1 anchored to edge and vertice sites is more reactive to the DielsAlder reaction than that involving terrace sites.Key words: monolayer protected cluster, site selective reactivity, DielsAlder, photochemistry.

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46

Lehmann, Thomas E., Gerhard Müller, and Albrecht Berkessel. "Photochemistry of 4‘-Benzophenone-Substituted Nucleoside Derivatives as Models for Ribonucleotide Reductases: Competing Generation of 3‘-Radicals and Photoenols." Journal of Organic Chemistry 65, no. 8 (April 2000): 2508–16. http://dx.doi.org/10.1021/jo991811s.

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47

Nakagaki, Ryoichi, Masaharu Yamaoka, and Kiyoshi Mutai. "Photochemistry of Bifunctional Chain Molecules Containing Benzophenone and Anilino Chromophores. Magnetic Field and Magnetic Isotope Effects on Lifetimes of Triplet Biradicals." Bulletin of the Chemical Society of Japan 72, no. 3 (March 1999): 347–55. http://dx.doi.org/10.1246/bcsj.72.347.

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48

Vieira Ferreira, L. F., J. C. Netto-Ferreira, I. V. Khmelinskii, A. R. Garcia, and Silvia M. B. Costa. "Photochemistry on Surfaces: Matrix Isolation Mechanisms Study of Interactions of Benzophenone Adsorbed on Microcrystalline Cellulose Investigated by Diffuse Reflectance and Luminescence Techniques." Langmuir 11, no. 1 (January 1995): 231–36. http://dx.doi.org/10.1021/la00001a040.

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49

Adam, Waldemar, Ulrike Kliem, and Vittorio Lucchini. "Preparative UV-VIS laser photochemistry: Photocycloadditions of methylenelactones with benzophenone andp-benzoquinone. Oxygen trapping of paterno-Büchi triplet 1,4-diradicals as model reactions for quinghaosu-type 1,2,4-trioxanes." Liebigs Annalen der Chemie 1988, no. 9 (September 14, 1988): 869–75. http://dx.doi.org/10.1002/jlac.198819880909.

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Dell’Amico, Luca, Javier Mateos, Sara Cuadros, and Alberto Vega-Peñaloza. "Unlocking the Synthetic Potential of Light-Excited Aryl Ketones: Applications in Direct Photochemistry and Photoredox Catalysis." Synlett, March 2, 2021. http://dx.doi.org/10.1055/a-1403-4613.

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Abstract:

AbstractIn this Account, we summarize the contributions of our group to the field of photochemistry and photocatalysis. Our work deals with the development of novel synthetic methods based on the exploitation of photoexcited aryl ketones. The application of new technologies, such as microfluidic photoreactors (MFPs), has enhanced the synthetic performance and scalability of several photochemical methods, e.g., Paternò–Büchi and photoenolization/Diels–Alder processes, while opening the way to unprecedented reactivity. In addition, careful mechanistic analysis of the developed methods has been instrumental in disclosing a new family of powerful organic photocatalysts that can mediate several thermodynamically extreme photoredox processes.1 Introduction1.1 Shining Light on Aryl Ketones: From the Historical Background to Recent Synthetic Applications1.2 Preliminary Mechanistic Considerations2 Synthetic Transformations Driven by Triplet State Benzophenones3 Synthetic Transformations Driven by Triplet State o-Alkyl-Substituted Benzophenones4 The Evolution of Aryl-Ketone-Derived Products: Applications in Organophotoredox Catalysis5 Conclusions and Future Directions

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