Cyclopropenone-caged Sondheimer diyne (dibenzo[a, e]cyclooctadiyne): a photoactivatable linchpin for efficient SPAAC crosslinking. Issue 3 (5th November 2015)

• Record Type: Journal Article
• Authors: Sutton, Dewey A.; Yu, Seok-Ho; Steet, Richard; Popik, Vladimir V.
• Is Part Of: Chemical communications. Volume 52:Issue 3(2016)
• Page Start: 553
• Page End: 556
• Publication Date: 2015-11-05
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c5cc08106h
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Photo double "click": Irradiation of bis-cyclopropenone-masked dibenzocyclooctadiynes with UVA or violet light allows for the efficient derivatization of azide-tagged substrates with azide-bearing functional moieties. 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.