The chemical inertness and structural complexity of lignin limit the synthesis and development of chiral lignin carbon dots (CLCDs). To address this problem, this study employed a Mannich reaction-mediated amination modification strategy to graft chiral amino acids onto lignin for synthesizing CLCDs. The obtained levorotatory and dextrorotatory lignin-derived carbon dots (L-LCDs and D-LCDs) exhibit the chiral signal at 237 nm inherited from the intrinsic chirality of tryptophan, while the induced chiral signal at 275 nm originates from structural integration between tryptophan and lignin frameworks. It was found that D-LCDs, as a fluorescent probe, exhibited exceptional selectivity towards d-asparagine (D-Asn) and d-glutamine (D-Gln) with limits of detection (LOD) for 0.07 mM and 0.09 mM, respectively. In addition, the hydrogen bonding interaction causes the L/D-LCDs immobilized on the filter paper strips to exhibit green room temperature phosphorescence (RTP). The introduction of Asn generates stronger hydrogen bonding interactions, increased steric hindrance and racemization effects, extending the afterglow time to 13 s and elevating the phosphorescence lifetime to 141.8 ms. Building upon this phosphorescence phenomenon, a dynamic information encryption system with time-resolved optical responses was successfully demonstrated on the filter paper matrix. As the first report on lignin-based chiral carbon dots, this work opens up a new avenue for the controlled preparation of carbon dots with clear chiral origins, and expands the application prospects of CLCDs in selective recognition and new class of bio-based responsive RTP materials.
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