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Electrochemical, EPR, and computational study of pyrene conjugates—precursors for novel type of organic semiconductors

Abstract

A series of nine precursors for pyrene-based biodegradable organic (semi)conductors having tetrasubstituted double bond as a central organic core and photo- or redox active centers attached at this core were investigated electrochemically in aprotic media at various electrodes. The influence of individual parts of the molecule on the redox properties were determined, the radical intermediates were intercepted using in situ EPR spectroelectrochemical experiments, the respective mechanisms were discussed, the difference between the first oxidation and the first reduction potential, respectively, were determined, and the experimental data were correlated with quantum chemical calculations.

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Acknowledgements

Computational resources were supplied by the project “e-Infrastruktura CZ” (e-INFRA LM2018140) provided within the program Projects of Large Research, Development, and Innovations Infrastructures.

Funding

The authors are grateful to the grant GAČR 18–12150 S for financial support.

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Correspondence to Jiří Ludvík.

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This contribution is dedicated to my good friend and colleague prof. Fritz Scholz with best wishes for further years.

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Koláčná, L., Klíma, J., Polák, P. et al. Electrochemical, EPR, and computational study of pyrene conjugates—precursors for novel type of organic semiconductors. J Solid State Electrochem 26, 503–514 (2022). https://doi.org/10.1007/s10008-021-05094-7

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  • DOI: https://doi.org/10.1007/s10008-021-05094-7

Keywords

  • Pyrene
  • Cyclobutene
  • Biodegradable organic semiconductors
  • Polarography
  • Cyclic voltammetry
  • In situ EPR spectroelectrochemistry
  • Ab initio calculations