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- W4387130531 abstract "Abstract One-pot synthesis of heterocyclic aromatics with good optical properties from phenolic β-O-4 lignin segments is of high importance to meet high value added biorefinery demands. However, executing this process remains a huge challenge due to the incompatible reaction conditions of the depolymerization of lignin β-O-4 segments containing γ-OH functionalities and bioresource-based aggregation-induced emission luminogens (BioAIEgens) formation with the desired properties. In this work, benzannulation reactions starting from lignin β-O-4 moieties with 3-alkenylated indoles catalyzed by vanadium-based complexes have been successfully developed, affording a wide range of functionalized carbazoles with up to 92% yield. Experiments and density functional theory calculations suggest that the reaction pathway involves the selective cleavage of double C-O bonds/Diels-Alder cycloaddition/dehydrogenative aromatization. Photophysical investigations show that these carbazole products represent a class of BioAIEgens with twisted intramolecular charge transfer. Distinctions of emission behavior were revealed based on unique acceptor-donor-acceptor-type molecular conformations as well as molecular packings. This work features lignin β-O-4 motifs with γ-OH functionalities as renewable substrates, without the need to apply external oxidant/reductant systems. Here, we show a concise and sustainable route to functional carbazoles with AIE properties, building a bridge between lignin and BioAIE materials." @default.
- W4387130531 created "2023-09-29" @default.
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- W4387130531 date "2023-09-28" @default.
- W4387130531 modified "2023-10-17" @default.
- W4387130531 title "Towards bioresource-based aggregation-induced emission luminogens from lignin β-O-4 motifs as renewable resources" @default.
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- W4387130531 doi "https://doi.org/10.1038/s41467-023-41681-0" @default.
- W4387130531 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/37770462" @default.
- W4387130531 hasPublicationYear "2023" @default.
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