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Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones.

Publication ,  Journal Article
Kean, ZS; Black Ramirez, AL; Yan, Y; Craig, SL
Published in: Journal of the American Chemical Society
August 2012

Force-induced transformations of polymer-bound functionalities have the potential to produce a rich array of stress-responsive behavior. One area of particular interest is the activation of non-scissile mechanophores in which latent reactivity can be unveiled that, under the appropriate conditions, could lead to constructive bond formation in materials exposed to typically destructive stress. Here, the mechanical activation of a bicyclo[3.2.0]heptane (BCH) mechanophore is demonstrated via selective labeling of bis-enone products. BCH ring-opening produces large local elongation (>4 Å) and products that are reactive to conjugate additions under mild conditions. Subsequent photocyclization regenerates the initial BCH functionality, providing switchable structure and reactivity along the polymer backbone in response to stress and visible light.

Duke Scholars

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

August 2012

Volume

134

Issue

31

Start / End Page

12939 / 12942

Related Subject Headings

  • Photochemical Processes
  • Molecular Structure
  • Mechanical Phenomena
  • Heptanes
  • General Chemistry
  • Cyclization
  • Click Chemistry
  • Catalysis
  • Bridged Bicyclo Compounds
  • 40 Engineering
 

Citation

APA
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ICMJE
MLA
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Kean, Z. S., Black Ramirez, A. L., Yan, Y., & Craig, S. L. (2012). Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones. Journal of the American Chemical Society, 134(31), 12939–12942. https://doi.org/10.1021/ja3063666
Kean, Zachary S., Ashley L. Black Ramirez, Yufan Yan, and Stephen L. Craig. “Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones.Journal of the American Chemical Society 134, no. 31 (August 2012): 12939–42. https://doi.org/10.1021/ja3063666.
Kean ZS, Black Ramirez AL, Yan Y, Craig SL. Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones. Journal of the American Chemical Society. 2012 Aug;134(31):12939–42.
Kean, Zachary S., et al. “Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones.Journal of the American Chemical Society, vol. 134, no. 31, Aug. 2012, pp. 12939–42. Epmc, doi:10.1021/ja3063666.
Kean ZS, Black Ramirez AL, Yan Y, Craig SL. Bicyclo[3.2.0]heptane mechanophores for the non-scissile and photochemically reversible generation of reactive bis-enones. Journal of the American Chemical Society. 2012 Aug;134(31):12939–12942.
Journal cover image

Published In

Journal of the American Chemical Society

DOI

EISSN

1520-5126

ISSN

0002-7863

Publication Date

August 2012

Volume

134

Issue

31

Start / End Page

12939 / 12942

Related Subject Headings

  • Photochemical Processes
  • Molecular Structure
  • Mechanical Phenomena
  • Heptanes
  • General Chemistry
  • Cyclization
  • Click Chemistry
  • Catalysis
  • Bridged Bicyclo Compounds
  • 40 Engineering