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

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....

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2018-07, Vol.23 (7), p.1758
Main Authors: Jobelius, Hannah, Wagner, Norbert, Schnakenburg, Gregor, Meyer, Andreas
Format: Article
Language:English
Subjects:
Antiferromagnetism
broken symmetry DFT
Case studies
Chemical modification
Chemistry
Cross coupling
Crystallography
Electron transfer
EPR spectroscopy
exchange coupling
Heterocyclic Compounds, 1-Ring - chemistry
Magnetic permeability
Magnetic susceptibility
Magnetism
Models, Chemical
Organic chemistry
Physical properties
Polymers - chemical synthesis
Polymers - chemistry
radicals
redox chemistry
Redox properties
X-ray crystallography
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules23071758