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Bright, “Clickable” Porphyrins for the Visualization of Oxygenation under Ambient Light
Author(s) -
Roussakis Emmanuel,
Li Zongxi,
Nowell Nicholas H.,
Nichols Alexander J.,
Evans Conor L.
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201506847
Subject(s) - click chemistry , oxygenation , naked eye , dendrimer , absorption (acoustics) , alkyne , chemistry , materials science , photochemistry , nanotechnology , combinatorial chemistry , organic chemistry , catalysis , ecology , chromatography , composite material , detection limit , biology
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.