Breaking strong alkynyl-phenyl bonds: poly(para-phenylene ethynylene)s under mechanical stress
Stronger chemical bonds withstand higher mechanical forces; thus, the rupture of single bonds is preferred over the rupture of double or triple bonds or aromatic rings. We investigated bond scission in poly(dialkyl-p-phenylene ethynylene)s (PPEs), a fully conjugated polymer. In a scale-bridging appr...
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| Hauptverfasser: | , , , , , , , , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
2024
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| In: |
Journal of the American Chemical Society
Year: 2024, Jahrgang: 146, Heft: 40, Pages: 27594-27599 |
| ISSN: | 1520-5126 |
| DOI: | 10.1021/jacs.4c08765 |
| Online-Zugang: | Verlag, kostenfrei, Volltext: https://doi.org/10.1021/jacs.4c08765
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| Verfasserangaben: | Maximilian Elter, Matthias Brosz, Daniel Sucerquia, Andrei Kuzhelev, Denis C. Kiesewetter, Markus Kurth, Andreas Dreuw, Thomas F. Prisner, Jan Freudenberg, Uwe H. F. Bunz, and Frauke Gräter |
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| 520 | |a Stronger chemical bonds withstand higher mechanical forces; thus, the rupture of single bonds is preferred over the rupture of double or triple bonds or aromatic rings. We investigated bond scission in poly(dialkyl-p-phenylene ethynylene)s (PPEs), a fully conjugated polymer. In a scale-bridging approach using electron-paramagnetic resonance spectroscopy and gel permeation chromatography of cryomilled samples, in combination with density functional theory calculations and coarse-grained simulations, we conclude that mechanical force cleaves the sp-sp2 bond of PPEs (bond dissociation energy as high as 600 kJ mol-1). Bond scission primarily occurs in shear bands with locally increased shear stresses. The scission occurs in the middle of the PPE chains. Breaking sp-sp2 bonds into free radicals thus is feasible but requires significant mechanical force and an efficient stress concentration. | ||
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