gem-Dichlorocyclopropanes as abundant and efficient mechanophores in polybutadiene copolymers under mechanical stress.


Journal Article

When gem-dichlorocyclopropane (gDCC) copolymers derived from polybutadiene are subjected to ultrasonication, the gDCCs undergo ring opening to form 2,3-dichloroalkenes. The reactivity is not observed in low-molecular-weight (6.5 kDa) copolymers or side-chain gDCCs, consistent with mechanically induced reactivity due to the elongational strain of the polymers in the sonication flow fields. The ring openings occur several hundred times more frequently than polymer chain scission, and cis-coupled gDCCs are slightly more likely to react than their trans isomers. The ability to dramatically and specifically alter the structure of the polymer backbone through a coupled restoring force suggests new routes to postsynthetic polymer modification and motivates the design of easily scalable mechanophores for applications in stress-responsive polymers.

Full Text

Duke Authors

Cited Authors

  • Lenhardt, JM; Black, AL; Craig, SL

Published Date

  • August 2009

Published In

Volume / Issue

  • 131 / 31

Start / End Page

  • 10818 - 10819

PubMed ID

  • 19603747

Pubmed Central ID

  • 19603747

Electronic International Standard Serial Number (EISSN)

  • 1520-5126

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja9036548


  • eng