Enhanced circularly polarized luminescence attained via self-assembly of heterochiral as opposed to homochiral dipeptides in water

与同手性二肽相比,异手性二肽在水中的自组装可增强圆偏振发光。

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Abstract

Circularly polarized luminescence (CPL) is gaining interest across various disciplines, including materials science, pharmaceuticals, and sensing technologies. Organic molecules, due to their ease of synthesis and reduced toxicity, are a focus for achieving high dissymmetry values (g (lum)) in CPL. Here, we present a low molecular weight molecule (1), a dipeptide (Ala-Phe) covalently linked with tetraphenyl-ethylene (TPE), an Aggregation-Induced Emission luminophore (AIE-gen). Varying the stereochemistry of amino acid chiral centers, we synthesized homochiral 1-(l, l) & 1-(d, d) and heterochiral 1-(l, d) and 1-(d, l). In aqueous media, these molecules exhibit aggregation-induced chirality at the TPE chromophore. Heterochiral systems form sheet-like structures, displaying a bisignate induced circular dichroism signal and a good g (lum) value for CPL [7.5 (±0.04) × 10(-3)]. Conversely, homochiral systems adopt fibrillar morphology, exhibiting a monosignate induced circular dichroism signal with a lower dissymmetry value for CPL [1.3 (±0.05) × 10(-3)]. This study introduces the concept of chiroptical amplification, emphasizing enhanced CPL through heterochiral peptide-induced CPL compared to its homochiral counterpart, with an ON and OFF CPL signal at low and high temperature respectively.

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