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

Novel methylthiophene/benzo[b]thiophene perylene bisimide thiol-precursors that would generate thiols via a green-light-induced (lambda(exc) = 530 nm, phi(re) = 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.

Automated summary

In this study, novel methylthiophene/benzo[b]thiophene perylene bisimide thiol-precursors were introduced, which would generate thiols via a green-light-induced photorearrangement. The photoreleased thiols enabled a subsequent thiol-ene click ligation with electron deficient substrates without the need for washing. Additionally, the intrinsic fluorescence evolution from the rearrangement of perylene bisimide scaffolds allowed for self-reporting of the entire thiol formation process, enhancing the versatility of applications.