Polystyrene Functionalized with Diarylacetonitrile for the Visualization of Mechanoradicals and Improved Thermal Stability.

The direct scission of polymer main chains leads to a decrease in the performance of the polymeric materials. Polystyrene-functionalized with diarylacetonitrile (DAAN) was prepared through a postpolymerization modification with 4-methoxymandelonitrile to generate mechanofluorescent polymers that enable the visualization of the scission of the polymer main chain. The polymeric mechanoradicals obtained from the homolytic cleavage of the polymer main chain in response to mechanical stress were observed using fluorescence and electron paramagnetic resonance spectroscopy. Moreover, a thermogravimetric analysis showed that the thermal stability of the polymers was greatly improved relative to the parent polystyrene, that is, the introduction of the DAAN moiety via postpolymerization modification endowed the original polymers with multiple functions in one step; specifically, the ability to visualize polymer main-chain scission and improved thermal stability.