Circularly Polarized Luminescence and Dynamic Regulation Based on the co-Assembly of L/D-Lysine Hydrochloride and Photoactivated AIE Molecules

doi:10.6023/A22010015

Acta Chimica Sinica ›› 2022, Vol. 80 ›› Issue (5): 647-651.DOI: 10.6023/A22010015 Previous Articles Next Articles

Article

基于L/D-赖氨酸盐酸盐和光活化AIE分子共组装实现圆偏振发光及动态调控

冯锡成^a, 朱亮亮^b, 岳兵兵^a^,^*()

a 上海理工大学材料与化学学院上海 200093
b 复旦大学高分子科学系聚合物分子工程国家重点实验室上海 200438

投稿日期:2022-01-10 发布日期:2022-05-31
通讯作者: 岳兵兵
基金资助:
上海市科技创新行动计划扬帆项目(20YF1432400); 国家自然科学基金(22105128)

Circularly Polarized Luminescence and Dynamic Regulation Based on the co-Assembly of L/D-Lysine Hydrochloride and Photoactivated AIE Molecules

Xicheng Feng^a, Liangliang Zhu^b, Bingbing Yue^a()

a School of Materials and Chemistry, University of Shanghai for Science and Technology, Shanghai 200093, China
b State Key Laboratory of Molecular Engineering of Polymers,Department of Macromolecular Science, Fudan University, Shanghai 200438, China

Received:2022-01-10 Published:2022-05-31
Contact: Bingbing Yue
Supported by:
Shanghai Sailing Program(20YF1432400); partially from the National Natural Science Foundation of China(22105128)

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Abstract

In recent years, chiral materials based on circularly polarized luminescence (CPL) generated by molecular assembly have developed rapidly. However, the overall CPL signal of organic material systems is still weak and lacks precise modulation means. As a non-contact external stimulus, light stimulation has the advantages of precision and speed. Therefore, in this work, hexathiobenzene (M-1) with photoactive aggregation-induced emission (AIE) properties were used as fluorescent dyes, and chiral amino acids L/D-Lysine hydrochloride (L/D-Lys) were used as chiral templates. Supramolecular L/D-Lys@M-1 components are formed by intermolecular hydrogen bonding in a mixed solvent (N,N-dimethylformamide (DMF)/H₂O). Specifically, 1 mmol/L M-1 and 6 mmol/L L/D-Lys were dissolved in 700 μL DMF. Next, add 300 μL ultra-pure water to the mixture at 60 ℃ and cool the solution to 25 ℃. Due to the formation of L/D-Lys@M-1 co-assembly, the transparent solution gradually becomes an opaque suspension. The photoluminescence spectra, UV absorption spectra and DLS (dynamic light scattering) were used to characterize the structure and photoluminescence properties of the photoluminescence components. It was found that L/D-Lys@M-1 had self-aggregation effect under the photoluminescence, its particle size increased from ca. 700 nm to ca. 1400 nm, and it produced continuously enhanced emission at 450 nm and 550 nm. The chiral properties of ground state and excited state were studied by CD (circular dichroism) and CPL. The Cotton effect was observed at 250 nm and 300 nm under solvent-induced and light-controlled conditions, and the CD intensity of the L/D-Lys@M-1 co-assembly system increased with prolonged illumination time, indicating that the co-assembly system realized chiral transfer and amplification. CPL spectra indicate that, under the solvent effect of poor solvent H₂O, the co-assembly induced CPL signal at 540 nm (M-1 molecule fluorescence emission), luminescent dissymmetry factor (|g_lum|) 0.3×10^-2. This study provides a strategy for CPL construction and dynamic regulation of achiral fluorescence molecules.

Key words: chiral assembly, supramolecular, photocontrol, circularly polarized luminescence (CPL)

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Xicheng Feng, Liangliang Zhu, Bingbing Yue. Circularly Polarized Luminescence and Dynamic Regulation Based on the co-Assembly of L/D-Lysine Hydrochloride and Photoactivated AIE Molecules[J]. Acta Chimica Sinica, 2022, 80(5): 647-651.

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Fig. & Tab. 6

Figure 1. Synthesis of M-1 and L-Lys@M-1

Figure 2. FT-IR spectra of L-Lys•HCl, M-1 and L-Lys@M-1

Figure 3. (a) Fluorescence spectra under continuous illumination, (b) UV-Vis spectra under continuous illumination, (c) DLS under continuous illumination and (d) fluorescence lifetime of L-Lys@M-1 (λex=365 nm)

Figure 4. Effects of (a) water content and (b) UV on CD spectra of L/D-Lys@M-1

Figure 5. SEM images of L-Lys@M-1 in (a) pure DMF, (b) mixed solvent (φH2O=30%) without UV and (c) mixed solvent (φH2O=30%) with 90 s UV

Figure 6. (a) The CPL spectra and (b) glum of L/D-Lys@M-1 in pure solvent DMF and mixed solvent DMF/H2O

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基于L/D-赖氨酸盐酸盐和光活化AIE分子共组装实现圆偏振发光及动态调控

Circularly Polarized Luminescence and Dynamic Regulation Based on the co-Assembly of L/D-Lysine Hydrochloride and Photoactivated AIE Molecules

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