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Verdazyls as Possible Building Blocks for Multifunctional Molecular Materials: A Case Study on 1,5-Diphenyl-3-(p-iodophenyl)-verdazyl Focusing on Magnetism, Electron Transfer and the Applicability of the Sonogashira-Hagihara Reaction

1
Institute of Physical and Theoretical Chemistry, University of Bonn, 53115 Bonn, Germany
2
Institute of Inorganic Chemistry, University of Bonn, 53121 Bonn, Germany
3
Max-Planck-Institute for Biophysical Chemistry, 37077 Göttingen, Germany
*
Author to whom correspondence should be addressed.
Molecules 2018, 23(7), 1758; https://doi.org/10.3390/molecules23071758
Received: 28 June 2018 / Revised: 15 July 2018 / Accepted: 16 July 2018 / Published: 18 July 2018
(This article belongs to the Special Issue Trityl Radicals: Synthesis, Properties and Applications)
This work explores the use of Kuhn verdazyl radicals as building blocks in multifunctional molecular materials in an exemplary study, focusing on the magnetic and the electron transfer (ET) characteristics, but also addressing the question whether chemical modification by cross-coupling is possible. The ET in solution is studied spectroscopically, whereas solid state measurements afford information about the magnetic susceptibility or the conductivity of the given samples. The observed results are rationalized based on the chemical structures of the molecules, which have been obtained by X-ray crystallography. The crystallographically observed molecular structures as well as the interpretation based on the spectroscopic and physical measurements are backed up by DFT calculations. The measurements indicate that only weak, antiferromagnetic (AF) coupling is observed in Kuhn verdazyls owed to the low tendency to form face-to-face stacks, but also that steric reasons alone are not sufficient to explain this behavior. Furthermore, it is also demonstrated that ET reactions proceed rapidly in verdazyl/verdazylium redox couples and that Kuhn verdazyls are suited as donor molecules in ET reactions. View Full-Text
Keywords: radicals; exchange coupling; cross-coupling; broken symmetry DFT; EPR spectroscopy; X-ray crystallography; redox chemistry radicals; exchange coupling; cross-coupling; broken symmetry DFT; EPR spectroscopy; X-ray crystallography; redox chemistry
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MDPI and ACS Style

Jobelius, H.; Wagner, N.; Schnakenburg, G.; Meyer, A. Verdazyls as Possible Building Blocks for Multifunctional Molecular Materials: A Case Study on 1,5-Diphenyl-3-(p-iodophenyl)-verdazyl Focusing on Magnetism, Electron Transfer and the Applicability of the Sonogashira-Hagihara Reaction. Molecules 2018, 23, 1758. https://doi.org/10.3390/molecules23071758

AMA Style

Jobelius H, Wagner N, Schnakenburg G, Meyer A. Verdazyls as Possible Building Blocks for Multifunctional Molecular Materials: A Case Study on 1,5-Diphenyl-3-(p-iodophenyl)-verdazyl Focusing on Magnetism, Electron Transfer and the Applicability of the Sonogashira-Hagihara Reaction. Molecules. 2018; 23(7):1758. https://doi.org/10.3390/molecules23071758

Chicago/Turabian Style

Jobelius, Hannah, Norbert Wagner, Gregor Schnakenburg, and Andreas Meyer. 2018. "Verdazyls as Possible Building Blocks for Multifunctional Molecular Materials: A Case Study on 1,5-Diphenyl-3-(p-iodophenyl)-verdazyl Focusing on Magnetism, Electron Transfer and the Applicability of the Sonogashira-Hagihara Reaction" Molecules 23, no. 7: 1758. https://doi.org/10.3390/molecules23071758

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