Multiphoton Activation of Photo-Strain-Promoted Azide Alkyne Cycloaddition “Click” Reagents Enables in Situ Labeling with Submicrometer Resolution

Irradiation of cyclopropenone-masked dibenzocyclooctynes with near-infrared pulses from a femtosecond laser triggers photodecarbonylation via nonresonant two- or three-photon excitation. Multiphoton-generated cyclooctynes undergo a SPAAC reaction with organic azides, yielding the expected triazoles....

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 139; no. 40; pp. 14029 - 14032
Main Authors McNitt, Christopher D, Cheng, Hazel, Ullrich, Susanne, Popik, Vladimir V, Bjerknes, Matthew
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 11.10.2017
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Summary:Irradiation of cyclopropenone-masked dibenzocyclooctynes with near-infrared pulses from a femtosecond laser triggers photodecarbonylation via nonresonant two- or three-photon excitation. Multiphoton-generated cyclooctynes undergo a SPAAC reaction with organic azides, yielding the expected triazoles. Multiphoton-triggered SPAAC (MP-SPAAC) enables high resolution 3-D photoclick derivatization of hydrogels and tissues.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.7b08472