Bright, “Clickable” Porphyrins for the Visualization of Oxygenation under Ambient Light

Abstract

A new group of “clickable” and brightly emissive metalloporphyrins has been developed for the visualization of oxygenation under ambient light with the naked eye. These alkynyl‐terminated compounds permit the rapid and facile synthesis of oxygen‐sensing dendrimers through azide–alkyne click chemistry. With absorption maxima overlapping with the wavelengths of common commercial laser sources, they are readily applicable to biomedical imaging of tissue oxygenation. An efficient synthetic methodology, featuring the stable trimethylacetyl (pivaloyl) protecting group, is described for their preparation. A paint‐on liquid bandage containing a new, click‐synthesized porphyrin dendrimer has been used to map oxygenation across an ex vivo porcine skin burn model.

Document Details

Document Type
Pub Defense Publication
Publication Date
Oct 29, 2015
Source ID
10.1002/ange.201506847

Entities

People

  • Alexander J. Nichols
  • Conor L Evans
  • Emmanuel Roussakis
  • Nicholas H. Nowell
  • Zongxi Li

Organizations

  • Air Force Office of Scientific Research
  • National Institutes of Health
  • National Science Foundation

Tags

Fields of Study

  • Chemistry

Readers

  • Chemistry (specifically Chemical Fluorescence)
  • Organic Chemistry
  • Trauma Surgery or Emergency Medicine.

Technology Areas

  • Biotechnology
  • Biotechnology - Cancer Biotech
  • Directed Energy