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

Org Lett. 2023 Feb 10;25(5):872-876. doi: 10.1021/acs.orglett.3c00101. Epub 2023 Jan 27.

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.