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Published on: August 19, 2012
Green-Light Responsive Perylene Bisimides for Atom-Economic Thiol Generation and Click-Ligation
Fang Zhang1, Zhiwei Zhang1, Long Deng1
1Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China.
Abstract:
Novel methylthiophene/benzo[b]thiophene perylene bisimide thiol-precursors that would generate thiols via a green-light-induced (λexc = 530 nm, φre = 0.33) photorearrangement are presented herein. The "no-wash", photoreleased thiols thus enabled a subsequent thiol-ene click ligation with electron-deficient substrates. Moreover, by virtue of the intrinsic fluorescence evolution from the rearrangement of perylene bisimide scaffolds, the whole process of thiol formation could be self-reported, further potentiating themselves with application versatilities.
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