Green-Light Responsive Perylene Bisimides for Atom-Economic Thiol Generation and Click-Ligation

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.

2,3-Diarylmaleate salts as a versatile class of diarylethenes with a full spectrum of photoactivity in water

“…[22][23][24][25][26][27] The photorearrangement with formation of bicyclic aromatics is a recently discovered transformation (Scheme 1A(c)) that is promising for various applications, including organic synthesis, 28-30 photopharmacology 31 and click-chemistry. 32 Water-soluble DAEs bearing solubilizing charged groups are in demand for various photopharmacological and biomedical applications (Scheme 1B). The only example of the Mallory reaction in aqueous solutions was reported for light-induced generation of a DNA/RNA intercalator by wDAE-1 with a protonated amidine substituent.…”

“…22–27 The photorearrangement with formation of bicyclic aromatics is a recently discovered transformation (Scheme 1A(c)) that is promising for various applications, including organic synthesis, 28–30 photopharmacology 31 and click-chemistry. 32…”

2,3-Diarylmaleate salts as a versatile class of diarylethenes with a full spectrum of photoactivity in water

“…[22][23][24][25][26][27] The photorearrangement with formation of bicyclic aromatics is a recently discovered transformation (Scheme 1Aс) that is promising for various applications, including organic synthesis, [28][29][30] photopharmacology 31 and click-chemistry. 32 Scheme 1. Water-soluble DAEs for various photopharmacological and biomedical applications.…”