Light-Driven Depolymerization of Native Lignin Enabled by Proton-Coupled Electron Transfer

Nguyen, Suong T.; Murray, Philip R.  D.; Knowles, Robert R.

doi:10.1021/acscatal.9b04813

Title: Light-Driven Depolymerization of Native Lignin Enabled by Proton-Coupled Electron Transfer

Journal Article · 12 December 2019 · ACS Catalysis

DOI: https://doi.org/10.1021/acscatal.9b04813 · OSTI ID:1597295

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Princeton Univ., NJ (United States); Princeton University
Princeton Univ., NJ (United States)

In this work, we report a catalytic, light-driven method for the redox-neutral depolymerization of native lignin biomass at ambient temperature. This transformation proceeds via a proton-coupled electron-transfer (PCET) activation of an alcohol O–H bond to generate a key alkoxy radical intermediate, which then facilitates the β-scission of a vicinal C–C bond. Of significance, this single-step depolymerization is driven solely by visible-light irradiation, requires no stoichiometric chemical reagents, and produces no stoichiometric waste. This method exhibits good efficiency and excellent selectivity for the activation and fragmentation of the β-O-4 linkage in the polymer backbone, even in the presence of numerous other PCET-active functional groups. The feasibility of this protocol in enabling the cleavage of the β-1 linkage in model lignin dimers was also demonstrated. These results provide further evidence that visible-light photocatalysis can serve as a viable method for the direct conversion of lignin biomass into valuable arene feedstocks.

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Research Organization:: Energy Frontier Research Centers (EFRC) (United States). Bioinspired Light-Escalated Chemistry (BioLEC); Princeton Univ., NJ (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22)

Grant/Contract Number:: SC0019370

OSTI ID:: 1597295

Journal Information:: ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 1 Vol. 10; ISSN 2155-5435

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Title: Light-Driven Depolymerization of Native Lignin Enabled by Proton-Coupled Electron Transfer

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