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Coordination compounds and complexes exhibit different colors, geometries, and magnetic behavior, depending on the metal atom/ion and ligands from which they are composed. In an attempt to explain the bonding and structure of coordination complexes, Linus Pauling proposed the valence bond theory, or VBT, using the concepts of hybridization and the overlapping of the atomic orbitals. According to VBT, the central metal atom or ion (Lewis acid) hybridizes to provide empty orbitals of suitable...
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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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Pre-Planarized Triphenylamine-Based Linear Mixed-Valence Charge-Transfer Systems.

Marcel Krug1, Nina Fröhlich2, Dominik Fehn3

  • 1Department of Chemistry and Pharmacy, Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Egerlandstrasse 3, 91058, Erlangen, Germany.

Angewandte Chemie (International Ed. in English)
|December 11, 2020
PubMed
Summary

Synthesized planarized triphenylamine dimers exhibit efficient electron self-exchange. Low reorganization energies at redox centers enhance electron transfer, crucial for molecular electronics and energy storage applications.

Keywords:
N-heterotrianguleneselectron transfermixed-valence compoundsoxidationradical cations

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Area of Science:

  • Molecular Chemistry
  • Supramolecular Chemistry
  • Electrochemistry

Background:

  • Triphenylamines are versatile redox-active building blocks.
  • Planarization of redox centers can influence electron transfer properties.
  • Understanding electron self-exchange is key for designing functional molecular materials.

Purpose of the Study:

  • To synthesize and characterize linear dimers of planarized triphenylamines.
  • To investigate the electron self-exchange process in their radical cations.
  • To evaluate the impact of low internal reorganization energy on electron transfer.

Main Methods:

  • X-ray crystallography for structural verification.
  • Electron paramagnetic resonance (EPR) spectroscopy.
  • Absorption spectroscopy.
  • (Time-dependent) density functional theory (TD-DFT) calculations.

Main Results:

  • Successful synthesis and structural confirmation of three linear dimers.
  • Observation of electron self-exchange between the two redox centers in radical cations.
  • Demonstration that low internal reorganization energies significantly impact electron transfer parameters.
  • Similar distance-dependence attenuation factors for super-exchange mechanisms compared to non-planarized systems.

Conclusions:

  • Planarized triphenylamine units facilitate efficient electron self-exchange.
  • Low reorganization energy is a critical factor for optimizing electron transfer in molecular systems.
  • These findings contribute to the design of advanced materials for molecular electronics and energy storage.