[60]Fullerene Supported on Silica and γ-Alumina Sensitized Photooxidation of Olefins: Chemical Evidence for Singlet Oxygen and Electron Transfer Mechanism

Georgios C. Vougioukalakis; Yiannis Angelis; John Vakros; George Panagiotou; Christos Kordulis; Alexis Lycourghiotis; Michael Orfanopoulos

doi:10.1055/s-2004-820041

LETTER

[60]Fullerene Supported on Silica and γ-Alumina Sensitized Photooxidation of Olefins: Chemical Evidence for Singlet Oxygen and Electron Transfer Mechanism

Georgios C. Vougioukalakis^a, Yiannis Angelis^a, John Vakros^b, George Panagiotou^b, Christos Kordulis^b, Alexis Lycourghiotis^b, Michael Orfanopoulos*^a
^a Department of Chemistry, University of Crete, 71409 Iraklion, Crete, Greece
Fax: +30(2810)393601; e-Mail: orfanop@chemistry.uoc.gr;
^b Department of Chemistry, University of Patras and Institute of Chemical Engineering and High-Temperature Chemical Processes (ICE/HT), 26500 Patras, Greece

Abstract

All articles of this category

Abstract

Fullerene C₆₀ supported on silica and γ-alumina (2% w/w C₆₀/SiO₂ and C₆₀/Al₂O₃) sensitizes the photooxidation of alkenes via singlet oxygen and/or electron transfer mechanism, depending on the solvent and the substrate.

Key words

heterogeneous photooxidations - fullerene C₆₀ - alkenes - singlet oxygen - electron transfer

Full Text

References

1a Arbogast JW. Darmanyan AP. Foote CS. Rubin Y. Diederich FN. Alvarez MM. Anz SJ. Whetten RL. J. Phys. Chem. 1991, 95: 11

1b Arbogast JW. Foote CS. J. Am. Chem. Soc. 1991, 113: 8886

2a Wasielewski MR. O’Neil MP. Lykke KR. Pellin MJ. Gruen DM. J. Am. Chem. Soc. 1991, 113: 2774

2b Fraelich MR. Weisman RB. J. Phys. Chem. 1993, 97: 11145

For singlet oxygen reviews see:

3a Stratakis M. Orfanopoulos M. Tetrahedron 2000, 56: 1595

3b Clennan EL. Tetrahedron 2000, 56: 9151

3c Jefford CW. Chem. Soc. Rev. 1993, 22: 59

3d Foote CS. Cleenan EL. Active Oxygen in Chemistry Foote CS. Valentine JS. Greenberg A. Liebman JF. Chapman and Hall; London: 1995. p.105-140

4a Ito O. Sasaki Y. Yoshikawa Y. Watanabe A. J. Phys. Chem. 1995, 99: 9838

4b Sasaki Y. Yoshikawa Y. Watanabe A. Ito O. J. Chem. Soc., Faraday Trans. 1995, 91: 2287

4c Fukuzumi S. Suenobu T. Patz M. Hirasaka T. Itoh S. Fujitsuka M. Ito O. J. Am. Chem. Soc. 1998, 120: 8060

5a Zhang X. Romero A. Foote CS. J. Am. Chem. Soc. 1993, 115: 11024

5b An Y.-Z. Viado AL. Arce M.-J. Rubin Y. J. Org. Chem. 1995, 60: 8330

5c Chronakis N. Vougioukalakis GC. Orfanopoulos M. Org. Lett. 2002, 4: 945

6a Orfanopoulos M. Kambourakis S. Tetrahedron Lett. 1994, 35: 1945

6b Tokuyama H. Nakamura E. J. Org. Chem. 1994, 59: 1135

6c Orfanopoulos M. Kambourakis S. Tetrahedron Lett. 1995, 36: 435

7a Jensen AW. Daniels C. J. Org. Chem. 2003, 68: 207

7b Nie B. Hasan K. Greaves MD. Rotello VM. Tetrahedron Lett. 1995, 36: 3617

7c Guhr KI. Greaves MD. Rotello VM. J. Am. Chem. Soc. 1994, 116: 5997

8 The photooxidation of benzene and cyclohexene by the use of C₆₀ and C₇₀, grafted on mesoporous FSM-16 as photosensitizers, was recenlty reported. See: Fukuoka A. Fujishima K. Chiba M. Yamagishi A. Inagaki S. Fukushima Y. Ichikawa M. Catal. Lett. 2000, 68: 241

9 Vakros J. Panagiotou G. Kordulis C. Lycourghiotis A. Vougioukalakis GC. Angelis Y. Orfanopoulos M. Catal. Lett. 2003, 89: 269

For experimental details of the above techniques see:

10a Georgiadu I. Papadopoulou Ch. Matralis HK. Voyiatzis GA. Lycourghiotis A. Kordulis Ch. J. Phys. Chem. B 1998, 102: 8459

10b Vakros J. Kordulis Ch. Lycourghiotis A. Langmuir 2002, 18: 417

11a Ramamurthy V. Lakshminarasimhan P. Grey PC. Johnston LJ. Chem. Commun. 1998, 2411

11b Stratakis M. Nencka R. Rabalakos C. Adam W. Krebs O. J. Org. Chem. 2002, 67: 8758

12a Ogilby PR. Foote CS. J. Am. Chem. Soc. 1983, 105: 3423

12b Hurst JR. Schuster GB. J. Am. Chem. Soc. 1983, 105: 5756

13 Eriksen J. Foote CS. J. Am. Chem. Soc. 1980, 102: 6083

14 Stephenson LM. Grdina MJ. Orfanopoulos M. Acc. Chem. Res. 1980, 13: 419

15 An Y.-Z. Chen CB. Anderson JL. Sigman DS. Foote CS. Rubin Y. Tetrahedron 1996, 52: 5179

16 Bartlett PD. Landis ME. J. Am. Chem. Soc. 1977, 99: 3033

17a Gollnick K. Schnatterer A. Tetrahedron Lett. 1984, 25: 185

17b Gollnick K. Schnatterer A. Tetrahedron Lett. 1984, 25: 2735