Visible-Light Actinometry and Intermittent Illumination as Convenient Tools to Study Ru(bpy)3Cl2 Mediated Photoredox Transformations

Scientific Reports

Volumn 5, Issue , 2015, Pages

  Pitre, Spencer P ^a   McTiernan, Christopher D ^a   Vine, Wyatt ^a   Dipucchio, Rebecca ^a   Grenier, Michel ^a   Scaiano, Juan C ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84947547294     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep16397     Document Type: Article

References (25)

1. Prier, C. K., Rankic, D. A., MacMillan, D. W. C. Visible light photoredox catalysis with transition metal complexes: Applications in organic synthesis. Chem. Rev. 113, 5322-5363 (2013).
2. Hoffmann, N. Homogeneous Photocatalytic Reactions with Organometallic and Coordination Compounds-Perspectives for Sustainable Chemistry. ChemSusChem 5, 352-371 (2012).
3. Nicewicz, D. A., Nguyen, T. M. Recent Applications of Organic Dyes as Photoredox Catalysts in Organic Synthesis. ACS Catal. 4, 355-360 (2014).
4. Juris, A. et al. Ru(II) polypyridine complexes: photophysics, photochemistry, eletrochemistry, and chemiluminescence. Coord. Chem. Rev. 84, 85-277 (1988).
5. Turro, N. J., Ramamurthy, V., Scaiano, J. C. Modern molecular photochemistry of organic molecules. 1-483 (University Science Publishers, 2010).
6. Pitre, S. P., McTiernan, C. D., Ismaili, H., Scaiano, J. C. Mechanistic insights and kinetic analysis for the oxidative hydroxylation of arylboronic acids by visible light photoredox catalysis: A metal-free alternative. J. Am. Chem. Soc. 135, 13286-13289 (2013).
7. McTiernan, C. D., Pitre, S. P., Scaiano, J. C. Photocatalytic Dehalogenation of Vicinal Dibromo Compounds Utilizing Sexithiophene and Visible-Light Irradiation. ACS Catal. 4, 4034-4039 (2014).
8. Pitre, S. P., McTiernan, C. D., Ismaili, H., Scaiano, J. C. Metal-free photocatalytic radical trifluoromethylation utilizing methylene blue and visible light irradiation. ACS Catal. 4, 2530-2535 (2014).
9. Yang, X.-J., Chen, B., Zheng, L.-Q., Wu, L.-Z., Tung, C.-H. Highly efficient and selective photocatalytic hydrogenation of functionalized nitrobenzenes. Green Chem. 16, 1082-1086 (2014).
10. Romero, N. A., Nicewicz, D. A. Mechanistic Insight into the Photoredox Catalysis of Anti-Markovnikov Alkene Hydrofunctionalization Reactions. J. Am. Chem. Soc. 136, 17024-17035 (2014).
11. Kuhn, H. J., Braslavsky, S. E., Schmidt, R. Chemical actinometry. Pure & Appl. Chem. 61, 187-210 (1989).
12. Burnett, G. M., Melville, H. W. Determination of the Velocity Coefficients for Polymerization Processes. I. The Direct Photopolymerization of Vinyl Acetate. Proc. R. Soc. London, Ser. A 189, 456-480 (1947).
13. Wasserman, H. H., Scheffer, J. R., Cooper, J. L. Singlet oxygen reactions with 9,10-diphenylanthracene peroxide. J. Am. Chem. Soc. 94, 4991-4996 (1972).
14. Bengough, W. I., Henderson, W. The kinetics of the polymerization of 2-vinyl pyridine. Trans. Faraday Soc. 61, 141-149 (1965).
15. Cowley, P. R. E. J., Melville, H. W. The Photo-Degradation of Polymethylmethacrylate. II. Evaluation of Absolute Rate Constants for a Depolymerization Reaction. Proc. R. Soc. London, Ser. A 211, 320-334 (1952).
16. Nicholson, A. E., Norrish, R. G. W. Polymerization of styrene at high pressures using the sector technique. Discuss. Faraday Soc. 22, 104-113 (1956).
17. Chu, H.-H., Wu, J.-D. Free-radical propagation rate coefficients for hydroxyalkyl methacrylates and cyclohexyl methacrylate. J. Polym. Res. 14, 201-206 (2007).
18. Montalti, M., Credi, A., Prodi, L., Gandolfi, M. T. Handbook of Photochemistry. Third edn, 601-616 (Taylor & Francis Group, 2006).
19. Hatchard, C. G., Parker, C. A. A new sensitive chemical actinometer. II. Potassium ferrioxalate as a standard chemical actinometer. Proc. R. Soc. London, Ser. A 325, 518-536 (1956).
20. Abdel-Shafi, A. A., Beer, P. D., Mortimer, R. J., Wilkinson, F. Photosensitized generation of singlet oxygen from ruthenium(II)-substituted benzoaza-crown-bipyridine complexes. Phys. Chem. Chem. Phys. 2, 3137-3144 (2000).
21. Heinrich, G., Schoof, S., Gusten, H. 9,10-diphenylanthracene as a fluorescence quantum yield standard. J. Photochem. 3, 315-320 (1974).
22. Wilkinson, F., McGarvey, D. J., Olea, A. F. Factors governing the efficiency of singlet oxygen production during oxygen quenching of singlet and triplet states of anthracene derivatives in cyclohexane solution. J. Am. Chem. Soc. 115, 12144-12151 (1993).
23. Olea, A. F., Wilkinson, F. Singlet Oxygen Production from Excited Singlet and Triplet States of Anthracene Derivatives in Acetonitrile. J. Phys. Chem. 99, 4518-4524 (1995).
24. Bovey, F. A. Macromolecules: an introduction to polymer science. 1-40 (Academic Press, INC., 1979).
25. Shukla, D., Ahearn, W. G., Farid, S. Chain Amplification in Photoreactions of N-Alkoxypyridinium Salts with Alcohols: Mechanism and Kinetics. J. Org. Chem. 70, 6809-6819 (2005).