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Issue 23, 2011
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Mechanochemically triggered bond formation in solid-state polymers

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Abstract

Polybutadiene was functionalized with dibromo-, dichloro-, and bromochloro-carbene to give gem-dihalocyclopropanated (gDHC) polymers, in which the gDHCs act as mechanically activated functional groups or mechanophores. The polymers were extruded to determine the mechanophore activity in the solid state. The extent of gDHC ring opening depends on both the polymer composition and the macroscopic shear stress, ranging from 6.0% to over 30% after an hour of extrusion. In addition, the 2,3-dibromoalkene formed from mechanical activation of the gem-dibromocyclopropane was found to undergo subsequent nucleophilic substitution by chloride in the solid state. The number of solid-state substitution reactions far exceeds the number of main-chain bonds broken, a finding with implications for the future use of mechanophores in self-strengthening or self-healing polymers.

Graphical abstract: Mechanochemically triggered bond formation in solid-state polymers

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Publication details

The article was received on 11 Nov 2010, accepted on 14 Jan 2011 and first published on 16 Feb 2011


Article type: Paper
DOI: 10.1039/C0JM03875J
Citation: J. Mater. Chem., 2011,21, 8460-8465
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    Mechanochemically triggered bond formation in solid-state polymers

    A. L. Black, J. A. Orlicki and S. L. Craig, J. Mater. Chem., 2011, 21, 8460
    DOI: 10.1039/C0JM03875J

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