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Professor Michael Orfanopoulos

web: http://www.chemistry.uoc.gr/organic
email: orfanop@chemistry.uoc.gr
office phone: +30 2810 54 5030
lab phone: +30 2810 54 5046

Research Interests
Full CV

Brief Biography

Michael Orfanopoulos, Professor, born in Patras, Greece; B.Sc. University of Patras (1971); M.Sc. University of Toledo (1976); Ph.D. Chemistry, Case Western Reserve University (1979); Postdoctoral fellow, Stanford University with Prof. H. S. Mosher (1979-81); Research Scientist at the National Centre of Scientific Research “Demokritos” Athens, Greece (1981-85); Research Scholar UCLA (Los Angeles ) with Prof. C. S. Foote, (1984-85); Faculty of Chemistry, University of Crete, Greece, (1985-present); Fulbright Fellow UCLA, (1993); Chairman, Department of Chemistry, University of Crete, (1994-98 ); Visiting Professor, Scripps Research Institute, La Jolla, California with Prof. K. C. Nicolaou, (2000); Visiting Professor, California Institute of Technology (Caltech), with Prof. R. H. Grubbs, (2006); Chairman, Department of Chemistry, University of Crete, (Sept. 2010-2014); Author or coauthor of over 120 original articles.

Representative Publications

1. Vougioukalakis, G. C.; Prassides, K.; Orfanopoulos, M. "Novel Open-Cage Fullerenes Having a 12-Membered-Ring Orifice: Removal of the Organic Addends from the Rim of the Orifice" Org. Lett. 2004, 6, 1245.
http://pubs.acs.org/doi/pdf/10.1021/ol049843b

2. Vougioukalakis, G. C.; Orfanopoulos, M. "Photoinduced Electron Transfer Reactivity of Aza[60]fullerene. Three Discrete Functionalization Pathways with a Single Substrate" J. Am. Chem. Soc. 2004, 126, 15956.
http://pubs.acs.org/doi/pdf/10.1021/ja045495x

3. Hatzimarinaki, M.; Roubelakis, M. M.; Orfanopoulos, M. "Biradical Intermediate in the [2 + 2] Photocycloaddition of Dienes and Alkenes to [60]Fullerene" J. Am. Chem. Soc. 2005, 127, 14182.
http://pubs.acs.org/doi/pdf/10.1021/ja053431w

4. Roubelakis, M. M.; Vougioukalakis, G. C.; Orfanopoulos, M. "Solvent-Dependent Changes in the Ene Reaction of RTAD with Alkenes: The Cyclopropyl Group as a Mechanistic Probe" Org. Lett. 2006, 8, 39.
http://pubs.acs.org/doi/pdf/10.1021/ol052342l

5. Vougioukalakis, G. C.; Lykakis, I. N.; Hatzimarinaki, M.; Orfanopoulos, M. "Reaction of Aza[60]fullerene Radical with Diphenylmethanes and Fluorenes: A Mechanistic Approach" J. Org. Chem. 2006, 71, 829.
http://pubs.acs.org/doi/pdf/10.1021/jo051838d

6. Hatzimarinaki, M.; Orfanopoulos, M. "Novel Methodology For The Preparation of Five , Seven , and Nine-Membered Fused Rings on C60" Org. Lett. 2006, 8, 1775.
http://pubs.acs.org/doi/pdf/10.1021/ol0600887

7. Lykakis, I. N.; Vougioukalakis, G. C.; Orfanopoulos, M. "Homogeneous Decatungstate Catalyzed Photooxygenation of Tetrasubstituted Alkenes: A Deuterium Kinetic Isotope Effect Study" J. Org. Chem. 2006, 71, 8740.
http://pubs.acs.org/doi/pdf/10.1021/jo061238u

8. Lykakis, I. N.; Tanielian, C.; Seghrouchni, R.; Orfanopoulos, M. "Mechanism of Decatungstate Photocatalyzed Oxygenation of Aromatic Alcohols. Part II. Kinetic Isotope Effects Studies" J. Mol. Cat. A 2007, 262, 176.
http://www.sciencedirect.com/...

9. Roubelakis, M. M.; Vougioukalakis, G. C.; Orfanopoulos, M. "Open-Cage Fullerene Derivatives Having 11-, 12- and 13-Membered-Ring Orifices: Chemical Transformations of the Organic Addends on the Rim of the Orifice" J. Org. Chem. 2007, 72, 6526.
http://pubs.acs.org/doi/pdf/10.1021/jo070796l

10. Tzirakis, M. D.; Lykakis, I. N.; Panagiotou, G.; Bourikas, K.; Lycourghiotis, A.; Kordulis, C.; Orfanopoulos, M. "Decatungstate Catalyst Supported on Silica and g-Alumina: Efficient Photocatalytic Oxidation of Benzyl Alcohols" J. Cat. 2007, 252, 178.
http://www.sciencedirect.com/...

11. Tzirakis, M. D.; Orfanopoulos, M. "Decatungstate-Mediated Radical Reactions of C60 with Substituted Toluenes and Anisoles: A New Photochemical Functionalization Strategy for Fullerenes" Org. Lett. 2008, 10, 873.
http://pubs.acs.org/doi/pdf/10.1021/ol7030125

12. Alberti, M. N.; Orfanopoulos, M. "The Cyclopropyl Group as a Hypersensitive Probe in the Singlet Oxygen Ene Reaction Mechanism" Org. Lett. 2008, 10, 2465.
http://pubs.acs.org/doi/pdf/10.1021/ol800759u

13. Vougioukalakis, G. C.; Roubelakis, M. M.; Alberti, M. N.; Orfanopoulos, M. "Solvent-Dependent Changes in the Triazolinedione-Alkene Ene Reaction Mechanism" Chem. Eur. J. 2008, 14, 9696.
http://www3.interscience.wiley.com/journal/121419132/abstract

14. Alberti, M. N.; Vassilikogiannakis, G.; Orfanopoulos, M. "Stereochemistry of the Singlet Oxygenation of Simple Alkenes: a Stereospecific Transformation" Org. Lett. 2008, 10, 3997.
http://pubs.acs.org/doi/pdf/10.1021/ol801488w

15. Tzirakis, M. D.; Orfanopoulos, M. "Acyl Radical Reactions in Fullerene Chemistry: Direct Acylation of [60]Fullerene through an Efficient Decatungstate-Photomediated Approach" J. Am. Chem. Soc. 2009, 131, 4063.
http://pubs.acs.org/doi/pdf/10.1021/ja808658b

16. Alberti, M. N.; Orfanopoulos, M. "Concerning the Reactivity of PTAD with Isomeric Dienes: The Mechanism of the Diels-Alder Cycloaddition" Org. Lett. 2009, 11, 1659.
http://pubs.acs.org/doi/pdf/10.1021/ol900363n

17. Tzirakis, M. D.; Alberti, M. N.; Nye, L. C.; Drewello, T.; Orfanopoulos, M. "One-step Synthesis of Fullerene Hydride C60H2 via Hydrolysis of Acylated Fullerenes" J. Org. Chem. 2010, 74, 5746.
http://pubs.acs.org/doi/abs/10.1021/jo900934j

18. Tzirakis, M. D.; Lykakis, I. N.; Orfanopoulos, M., "Decatungstate as an Efficient Photocatalyst in Organic Chemistry" Chem. Soc. Rev. 2009, 28, 2609.
http://www.rsc.org/publishing/journals/CS/article.asp?doi=b812100c

19. Alberti, M. N.; Vougioukalakis, G. C.; Orfanopoulos, M. "Photosensitized Oxidations of Substituted Pyrroles: Unanticipated Radical-Derived Oxygenated Products" J. Org. Chem. 2009, 74, 7274.
http://pubs.acs.org/doi/pdf/10.1021/jo9012942

20. Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. "Open-Cage Fullerenes: Towards the Construction of Nanosized Molecular Containers" Chem. Soc. Rev. 2010, DOI: 10.1039/B913766A.
http://pubs.rsc.org/en/Content/ArticleLanding/2010/CS/B913766A

21. Alberti, M. N.; Orfanopoulos, M. "Recent Mechanistic Insights in the Singlet Oxygen Ene Reaction" Synlett 2010, 999.
https://www.thieme-connect.com/ejournals/abstract/synlett/doi/10.1055/s-0029-1219790

22. Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. "Radical Reactivity of Aza[60]fullerene: Preparation of Monoadducts and Limitations" J. Org. Chem. 2010, 75, 4124.
http://pubs.acs.org/doi/full/10.1021/jo100277v

23. Tzirakis, M. D.; Orfanopoulos, M. "Photochemical Addition of Ethers to C-60: Synthesis of the Simplest [60]Fullerene/Crown Ether Conjugates" Angew. Chem., Int. Ed. Engl. 2010, 49, 5891.
http://onlinelibrary.wiley.com/doi/10.1002/...

24. Alberti, M. N.; Orfanopoulos, M. "Unraveling the Mechanism of the Singlet Oxygen Ene Reaction: Recent Computational and Experimental Approaches" Chem. Eur. J. 2010, 16, 9414.
http://onlinelibrary.wiley.com/doi/10.1002/chem.201000752/abstract

25. Tzirakis, M. D.; Alberti, M. N.; Orfanopoulos, M. "Hydroxyalkylation of [60]fullerene: free radical addition of alcohols to C60" Chem. Commun. 2010, DOI: CC-COM-07-2010-002836.

26. Tzirakis, M. D.; Alberti, M. N.; Orfanopoulos, M. .Photocycloaddition of Biscyclopropyl Alkenes to C60: An Unprecedented Approach towards cis-1 Tricyclic-Fused Fullerenes. Org. Lett. 2011, 13, 3364-3368. DOI: 10.1021/ol201112a

27. Tzirakis, M. D.; Orfanopoulos, M. .Radical Reactions of Fullerenes: From Synthetic Organic Chemistry to Materials Science and Biology. CHEMICAL REVIEWS 113 (7): 5262-5321 (2013). DOI: 10.1021/cr300475r

28. Kellner, I. D.; Nye, L. C.; von Gernler, M. S.; Li, J.; Tzirakis, M. D.; Orfanopoulos, M.; Drewello, T. .Ion Formation Pathways of Crown Ether-Fullerene Conjugates in the Gas Phase.. Phys. Chem. Chem. Phys. 2014, 18982.18992. DOI: 10.1039/C4CP02374A