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Updated: Oct 8, 2025
Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Combining Hydroxyl-Yne and Thiol-Ene Click Reactions to Facilely Access Sequence-Defined Macromolecules for
1State Key Laboratory of Luminescent Materials and Devices, Guangdong Provincial Key Laboratory of Luminescence from Molecular Aggregates, AIE Institute, Center for Aggregation-Induced Emission, South China University of Technology, Guangzhou 510640, People's Republic of China.
Abstract:
Through mimicking the synthesis of hereditary-information-containing nucleic acids, scientists are committed to synthesizing sequence-defined macromolecules. Herein, a protecting-group-free, metal-free, and atom-economical chemistry combining hydroxyl-yne and thiol-ene click reactions was developed to efficiently synthesize sequence-defined oligo(monothioacetals) (overall yield of 54% for an 11-step synthesis) from readily available starting compounds and monomers under ambient conditions. The sequences of linear oligo(monothioacetals) could be easily decoded via a tandem ESI-MS/MS technique, making them new kinds of digital macromolecules with a high data storage density (0.013 bit/Da). Moreover, star oligo(monothioacetals) could also be facilely generated through divergent and convergent strategies and their combination. An unprecedented sequence-defined miktoarm star oligo(monothioacetal) was obtained, which could serve as a new nonlinear digital macromolecule to achieve 2D information matrix encoding and hold great potential to be applied for information encryption, anticouterfeiting, secret communication, etc. Thus, this work provides a powerful stepwise iterative approach to facilely access sequence-defined linear and topological oligo(monothioacetals) for high-density data storage.
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