Full Paper

Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry

  1. Jens Tüxen1,
  2. Sandra Eibenberger2,
  3. Stefan Gerlich2,
  4. Markus Arndt2,
  5. Marcel Mayor1,3

Article first published online: 13 JUL 2011

DOI: 10.1002/ejoc.201100638

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2011, Issue 25, pages 4823–4833, September 2011

Additional Information

How to Cite

Tüxen, J., Eibenberger, S., Gerlich, S., Arndt, M. and Mayor, M. (2011), Highly Fluorous Porphyrins as Model Compounds for Molecule Interferometry. Eur. J. Org. Chem., 2011: 4823–4833. doi: 10.1002/ejoc.201100638

Author Information

  1. 1

    Department of Chemistry, University of Basel, St. Johannsring 19, 4056 Basel, Switzerland, Fax: +41-61-267-1016

  2. 2

    University of Vienna, Vienna Center for Quantum Science and Technology, VCQ, Faculty of Physics, Boltzmanngasse 5, 1090 Vienna, Austria

  3. 3

    Karlsruhe Institute of Technology (KIT), Institute for Nanotechnology, P. O. Box 3640, 76021 Karlsruhe, Germany

Publication History

  1. Issue published online: 23 AUG 2011
  2. Article first published online: 13 JUL 2011
  3. Manuscript Received: 7 MAY 2011

Funded by

  • Swiss National Science Foundation
  • NCCR “Nanoscale Science”
  • ESF EuroCore Program MIME. Grant Number: I146-N16
  • Austrian FWF Wittgenstein. Grant Number: Z149-N16
  • CoQuS. Grant Number: W1210-N16

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Keywords:

  • Fluorine;
  • Aromatic substitution;
  • Mass spectrometry;
  • Heterocycles;
  • Quantum interference

Abstract

The synthesis and characterization of seven tailor-made highly fluorous porphyrin derivatives are described, as large perfluoroalkyl-functionalized organic molecules are the most complex objects for which the quantum wave nature has been observed so far. We have found, in particular, that tetrakis(pentafluorophenyl)porphyrin is a suitable starting point for a modular synthesis that is geared towards porphyrin derivatives with many peripheral fluorous chains. This allows us to tailor and optimize the sublimation features of these compounds for molecule interferometry. We have analyzed the evaporation process of one member of the series by determining the enthalpy of evaporation, as the creation of a sufficiently intense, slow molecular beam is crucial for quantum interference experiments. We present the quantum fringe pattern of a second member of the series, which we could obtain in a Kapitza–Dirac–Talbot–Lau interferometer.

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