Communication

A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5†

  1. Dr. Igor V. Kuvychko1,
  2. Sarah N. Spisak3,
  3. Dr. Yu-Sheng Chen2,
  4. Dr. Alexey A. Popov4,*,
  5. Prof. Marina A. Petrukhina3,*,
  6. Prof. Steven H. Strauss1,*,
  7. Dr. Olga V. Boltalina1,*

Article first published online: 11 APR 2012

DOI: 10.1002/anie.201200178

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 51, Issue 20, pages 4939–4942, May 14, 2012

Additional Information

How to Cite

Kuvychko, I. V., Spisak, S. N., Chen, Y.-S., Popov, A. A., Petrukhina, M. A., Strauss, S. H. and Boltalina, O. V. (2012), A Buckybowl with a Lot of Potential: C5-C20H5(CF3)5. Angew. Chem. Int. Ed., 51: 4939–4942. doi: 10.1002/anie.201200178

Author Information

  1. 1

    Department of Chemistry, Colorado State University, Fort Collins, CO 80523 (USA)

  2. 2

    ChemMatCARS/Center for Advanced Radiation Sources, University of Chicago @ Advanced Photon Source (USA)

  3. 3

    Department of Chemistry, University at Albany, State University of New York, Albany, NY 12222 (USA)

  4. 4

    Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)

*Department of Electrochemistry and Conducting Polymers, Leibniz Institute for Solid State and Materials Research, 01069 Dresden (Germany)

  1. †

    We thank the U.S. NSF (CHE-1012468 (OVB/SHS) and CHE-0546945 (M.A.P.)) for financial support and Prof. L. Dunsch for his continuing support. ChemMatCARS Sector15 is principally supported by the NSF/DOE (NSF/CHE-0822838). Use of the APS was supported by the U.S. DOE, Office of Science, Office of Basic Energy Sciences under contract DE-AC02-06CH11357.

Publication History

  1. Issue published online: 8 MAY 2012
  2. Article first published online: 11 APR 2012
  3. Manuscript Revised: 20 FEB 2012
  4. Manuscript Received: 9 JAN 2012

Funded by

  • U.S. NSF. Grant Numbers: CHE-1012468, CHE-0546945
  • NSF/DOE. Grant Number: NSF/CHE-0822838
  • U.S. DOE, Office of Science, Office of Basic Energy Sciences. Grant Number: DE-AC02-06CH11357

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Keywords:

  • corannulene;
  • density functional calculations;
  • electrochemistry;
  • fluorinated compounds;
  • X-ray diffraction
Thumbnail image of graphical abstract

Lots of potential: A trifluoromethylated corannulene, C5-C20H5(CF3)5, has been prepared and characterized spectroscopically and by X-ray crystallography. The structure exhibits a highly ordered bowl stacking that is unusual for corannulenes with acyclic substituents. The first reduction of C5-C20H5(CF3)5 is anodically shifted by 0.95 V, making it the strongest corannulene-based electron acceptor to date.

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