Chemical signal activation of an organocatalyst enables control over soft material formation

Nat Commun. 2017 Oct 12;8(1):879. doi: 10.1038/s41467-017-00998-3.

Abstract

Cells can react to their environment by changing the activity of enzymes in response to specific chemical signals. Artificial catalysts capable of being activated by chemical signals are rare, but of interest for creating autonomously responsive materials. We present an organocatalyst that is activated by a chemical signal, enabling temporal control over reaction rates and the formation of materials. Using self-immolative chemistry, we design a deactivated aniline organocatalyst that is activated by the chemical signal hydrogen peroxide and catalyses hydrazone formation. Upon activation of the catalyst, the rate of hydrazone formation increases 10-fold almost instantly. The responsive organocatalyst enables temporal control over the formation of gels featuring hydrazone bonds. The generic design should enable the use of a large range of triggers and organocatalysts, and appears a promising method for the introduction of signal response in materials, constituting a first step towards achieving communication between artificial chemical systems.Enzymes regulated by chemical signals are common in biology, but few such artificial catalysts exist. Here, the authors design an aniline catalyst that, when activated by a chemical trigger, catalyses formation of hydrazone-based gels, demonstrating signal response in a soft material.

Publication types

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

MeSH terms

  • Aniline Compounds / chemistry*
  • Catalysis / drug effects
  • Hydrazones / chemical synthesis*
  • Hydrogen Peroxide / chemistry*
  • Models, Molecular
  • Molecular Structure
  • Proof of Concept Study

Substances

  • Aniline Compounds
  • Hydrazones
  • Hydrogen Peroxide
  • aniline