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Experimental and DFT Studies of the Electron-Withdrawing Ability of Perfluoroalkyl (RF) Groups: Electron Affinities of PAH(RF)n Increase Significantly with Increasing R F Chain Length

Journal Article · · Chemistry - A European Journal
 [1];  [2];  [2];  [3];  [1];  [2];  [3];  [4];  [1];  [1]
  1. Department of Chemistry, Colorado State University, Fort Collins Colorado 80523 USA
  2. Department of Chemistry, University at Albany, State University of New York, Albany New York 12222 USA
  3. Physical Sciences Division, Pacific Northwest National Laboratory, MS K8 88, P.O. Box 999 Richland Washington 99352 USA
  4. Department of Electrochemistry and Conducting Polymers, Liebniz Institute for Solid State and Materials Research, Dresden 01069 Germany
+ Show Author Affiliations

Two series of aromatic compounds with perfluoroalkyl (RF) groups of increasing length, 1,3,5,7-naphthalene(RF)4 and 1,3,5,7,9-corannulene(RF)5, have been prepared and their electronic properties studied by low-temperature PES (i.e., gas-phase electron affinity (EA) measurements). These and many related compounds were also studied by DFT calculations. The data demonstrate unambiguously that the electron-withdrawing ability of RF substituents increases significantly and uniformly from CF3 to C2F5 to n-C3F7 to n-C4F9.

Research Organization:
Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Environmental Molecular Sciences Lab. (EMSL)
Sponsoring Organization:
USDOE
DOE Contract Number:
AC05-76RL01830
OSTI ID:
1439682
Report Number(s):
PNNL-SA-129788; 50069; KC0301050
Journal Information:
Chemistry - A European Journal, Vol. 24, Issue 6; ISSN 0947-6539
Publisher:
ChemPubSoc Europe
Country of Publication:
United States
Language:
English

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