Synthesis, Solubilization, and Photophysical Properties of Polyfluorinated Pentacene Dimers

Schroeder ZW, Greißel P, Wollny AS, Cross AJ, Chen L, Plny GF, Muller V, Hall AL, Blaskovits JT, Guldi DM, Tykwinski RR (2026)

Publication Type: Journal article

Publication year: 2026

Journal

Journal of Physical Organic Chemistry Wiley-Blackwell

Book Volume: 39

Article Number: e70086

Journal Issue: 7

DOI: 10.1002/poc.70086

Abstract

A polyfluorinated pentacene dimer, linked with a 1,3-diethynylphenylene spacer, was synthesized to investigate the effects of fluorination on the dynamics of singlet fission (SF). The incorporation of bulky 4,6-substituents on the phenylene spacer was necessary to improve the solubility of the fluorinated dimers, toward easier purification and analysis. Photophysical characterization shows that the incorporation of fluorine at the peripheral positions of the pentacene moieties inhibits the solvent dependence of the excited state observed in a nonfluorinated pentacene reference compound. Computational analysis suggests that fluorination drives efficient intramolecular π-stacking, limiting conformational flexibility. The results confirm that the reduction of polarizability and rotational freedom of the pentacene groups, imposed by fluorination, eliminates the influence of solvent polarity on singlet fission kinetics. The kinetic stability of the fluorinated and nonfluorinated dimers toward photosensitized endoperoxidation with O2 is also assessed and shows that SF contributes to the stability of nonfluorinated pentacenes, but not necessarily to the stability of their fluorinated counterparts.

Authors with CRIS profile

Phillip Greißel Lehrstuhl für Physikalische Chemie I Anna-Sophie Wollny Lehrstuhl für Physikalische Chemie I

Involved external institutions

University of Alberta CA Canada (CA)

How to cite

APA:

Schroeder, Z.W., Greißel, P., Wollny, A.-S., Cross, A.J., Chen, L., Plny, G.F.,... Tykwinski, R.R. (2026). Synthesis, Solubilization, and Photophysical Properties of Polyfluorinated Pentacene Dimers. Journal of Physical Organic Chemistry, 39(7). https://doi.org/10.1002/poc.70086

MLA:

Schroeder, Zachary W., et al. "Synthesis, Solubilization, and Photophysical Properties of Polyfluorinated Pentacene Dimers." Journal of Physical Organic Chemistry 39.7 (2026).

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