Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking

Dewey A. Sutton; Seok-Ho Yu; Richard Steet; Vladimir V. Popik

doi:10.1039/C5CC08106H

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Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking†

Dewey A. Sutton,^a Seok-Ho Yu,^b Richard Steet

^b and Vladimir V. Popik*^a

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* Corresponding authors

^a Department of Chemistry, University of Georgia, Athens, USA
E-mail: vpopik@uga.edu

^b Complex Carbohydrate Research Center, University of Georgia, Athens, USA

Abstract

The first fully conjugated bis-cyclopropenone (photo-DIBOD), a derivative of dibenzo[a,e][8]annulene, has been synthesized. 350–420 nm irradiation of this robust compound results in the efficient formation of dibenzo [a,e] cyclooctadiyne, an unstable, but useful SPAAC cross-linking reagent. Since photo-DIBO doesn't react with organic azides, this method allows for the spatiotemporal control of the ligation of two azide-tagged substrates.

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DOI: https://doi.org/10.1039/C5CC08106H
Article type: Communication
Submitted: 28 Sep 2015
Accepted: 02 Nov 2015
First published: 02 Nov 2015

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Chem. Commun., 2016,52, 553-556

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Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking

D. A. Sutton, S. Yu, R. Steet and V. V. Popik, Chem. Commun., 2016, 52, 553 DOI: 10.1039/C5CC08106H

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Chemical Communications

Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking†

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Cyclopropenone-caged Sondheimer diyne (dibenzo[a,e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking

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