C20H4(C4F8)3: A fluorine-containing annulated corannulene that is a better electron acceptor than C60

Angewandte Chemie - International Edition

Volumn 52, Issue 29, 2013, Pages 7505-7508

  Kuvychko, Igor V ^a   Dubceac, Cristina ^b   Deng, Shihu H M ^d   Wang, Xue Bin ^d   Granovsky, Alexander A ^e   Popov, Alexey A ^c   Petrukhina, Marina A ^b   Strauss, Steven H ^a   Boltalina, Olga V ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

^b STATE UNIVERSITY OF NEW YORK   (United States)

^c IFW DRESDEN   (Germany)

^d PACIFIC NORTHWEST NATIONAL LABORATORY   (United States)

^e Firefly Project   (Russian Federation)

Author keywords

annulation; corannulene; electron acceptors; perfluoroalkyl iodide; radical reactions

Indexed keywords

ANNULATION; CORANNULENE; ELECTRON ACCEPTOR; PERFLUOROALKYL IODIDE; RADICAL REACTIONS;

REACTION KINETICS;

PHOTOELECTRON SPECTROSCOPY;

EID: 84880121071     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201300796     Document Type: Article

References (25)

1. J. E. Anthony, Chem. Mater. 2011, 23, 583-590
2. T. Okamoto, K. Nakahara, A. Saeki, S. Seki, J. H. Oh, H. B. Akkerman, Z. N. Bao, Y. Matsuo, Chem. Mater. 2011, 23, 1646-1649
3. C.-P. Chen, S.-H. Chan, T.-C. Chao, C. Ting, B.-T. Ko, J. Am. Chem. Soc. 2008, 130, 12828-12833.
4. J. E. Anthony, A. Facchetti, M. Heeney, S. R. Marder, X. W. Zhan, Adv. Mater. 2010, 22, 3876-3892
5. H. Usta, A. Facchetti, T. J. Marks, Acc. Chem. Res. 2011, 44, 501-510.
6. Y. C. Chang, M. Y. Kuo, C. P. Chen, H. F. Lu, I. Chao, J. Phys. Chem. C 2010, 114, 11595-11601.
7. W. E. Barth, R. G. Lawton, J. Am. Chem. Soc. 1966, 88, 380-381.
8. H. Sakurai, T. Daiko, T. Hirao, Science 2003, 301, 1878.
9. G. Chen, R. G. Cooks, E. Corpuz, L. T. Scott, J. Am. Soc. Mass Spectrom. 1996, 7, 619-627.
10. Y.-T. Wu, J. S. Siegel, Chem. Rev. 2006, 106, 4843-4867
11. A. Sygula, Eur. J. Org. Chem. 2011, 1611-1625
12. V. M. Tsefrikas, L. T. Scott, Chem. Rev. 2006, 106, 4868-4884.
13. A. M. Butterfield, B. Gilomen, J. S. Siegel, Org. Process Res. Dev. 2012, 16, 664-676.
14. I. V. Kuvychko, S. N. Spisak, Y. S. Chen, A. A. Popov, M. A. Petrukhina, S. H. Strauss, O. V. Boltalina, Angew. Chem. 2012, 124, 5023-5026
15. Angew. Chem. Int. Ed. 2012, 51, 4939-4942.
16. B. M. Schmidt, S. Seki, B. Topolinski, K. Ohkubo, S. Fukuzumi, H. Sakurai, D. Lentz, Angew. Chem. 2012, 124, 11548-11551
17. Angew. Chem. Int. Ed. 2012, 51, 11385-11388.
18. 3, Z=4, T=120(2) K, 59 235 reflections, 6818 independent reflections, 560 parameters, R1(I>2σ(I))=0.0688, wR2=0.1726, Bruker APEX-II CCD diffractometer with a Mo-Kα X-ray tube source and graphite monochromator. A semiempirical absorption correction was applied using SCALE. Refined using SHELXL-97. CCDC 930358 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
19. M. A. Petrukhina, K. W. Andreini, J. Mack, L. T. Scott, J. Org. Chem. 2005, 70, 5713-5716.
20. A. A. Granovsky, Firefly version 8.0.0, http://classic.chem.msu.su/gran/ firefly/index.html
21. S. Grimme, J. Antony, S. Ehrlich, H. Krieg, J. Chem. Phys. 2010, 132, 154104
22. D. N. Laikov, Y. A. Ustynyuk, Russ. Chem. Bull. Int. Ed. 2005, 54, 820-826.
23. B. F. Malichenko, G. A. Yangol, L. I. Zamulina, Zh. Org. Khim. 1975, 11, 2118-2122.
24. X. B. Wang, H. K. Woo, L. S. Wang, J. Chem. Phys. 2005, 123, 051106-051101.
25. T. Liu, A. Troisi, Adv. Mater. 2013, 25, 1038-1041.