High density orthogonal surface immobilization via photoactivated copper-free click chemistry

J Am Chem Soc. 2010 Aug 18;132(32):11024-6. doi: 10.1021/ja105066t.

Abstract

Surfaces containing reactive ester polymer brushes were functionalized with cyclopropenone-masked dibenzocyclooctynes for the light activated immobilization of azides using catalyst-free click chemistry. The photodecarbonylation reaction in the amorphous brush layer is first order for the first 45 s with a rate constant of 0.022 s(-1). The catalyst-free cycloaddition of surface bound dibeznocyclooctynes proceeds rapidly in the presence of azides under ambient conditions. Photolithography using a shadow mask was used to demonstrate patterning with multiple azide containing molecules. This surface immobilization strategy provides a general and facile platform for the generation of multicomponent surfaces with spatially resolved chemical functionality.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Azides / chemistry
  • Copper / chemistry*
  • Cyclopropanes / chemistry
  • Esters
  • Light
  • Photochemical Processes*
  • Polymers / chemistry
  • Spectrum Analysis
  • Surface Properties

Substances

  • Azides
  • Cyclopropanes
  • Esters
  • Polymers
  • cyclopropenone
  • Copper