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Dioxetane scission products unchanged by mechanical force.

Jess M Clough1, Rint P Sijbesma

  • 1Laboratory of Macromolecular and Organic Chemistry, Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands).

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|August 23, 2014
PubMed
Summary

Mechanoluminescent polymers emit light when stressed, offering insights into material behavior. Mechanical force breaking dioxetanes yields similar products to thermal activation, suggesting a shared scission pathway.

Keywords:
chemiluminescencedioxetaneluminescencemechanochemistrypolymers

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Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Physical Chemistry

Background:

  • Mechanoluminescence (ML) from dioxetane-based polymers provides a novel method for stress characterization.
  • Understanding the scission products of ML is crucial for designing sensitive probes.

Purpose of the Study:

  • To investigate the scission products of dioxetane-based polymers under mechanical force.
  • To compare these products with those from thermal activation.
  • To elucidate the mechanism of force-induced dioxetane scission.

Main Methods:

  • Mechanical force was applied to induce light emission in dioxetane-based polymers.
  • Products of mechanical scission were analyzed and compared to thermally activated products.
  • A sensitized relay scheme was employed for reproducible detection of short-lived triplet products.

Main Results:

  • Mechanical breaking of dioxetanes produced strikingly similar scission products to thermal activation.
  • The singlet/triplet ratio was determined to be 1:9.9, with a total quantum yield of 9.8%.
  • High reproducibility in detecting short-lived triplet products was achieved.

Conclusions:

  • The similarity in scission products suggests a common pathway for both mechanical and thermal dioxetane scission.
  • Mechanical force releases steric hindrance, initiating a process analogous to thermal activation.
  • Excited states form post-transition state, explaining the conserved product distribution.