Citation: Yimeng Sun, Yuqian Jiang, Jian Jiang, Tiesheng Li, Minghua Liu. Keto-form directed hierarchical chiral self-assembly of Schiff base derivatives with amplified circularly polarized luminescence[J]. Chinese Chemical Letters, ;2024, 35(1): 108409. doi: 10.1016/j.cclet.2023.108409 shu

Keto-form directed hierarchical chiral self-assembly of Schiff base derivatives with amplified circularly polarized luminescence

Yimeng Sun ^a ,
Yuqian Jiang ^b ,
Jian Jiang ^{b, *,} ,
Tiesheng Li ^{a, *,} ,
Minghua Liu ^{a, c, d, *,}

a.
Green Catalysis Center, and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
b.
Key Laboratory of Nanosystem and Hierarchical Fabrication, CAS Center for Excellence in Nanoscience, National Center for Nanoscience and Technology, Beijing 100190, China
c.
National Laboratory for Molecular Science (BNLMS), CAS Laboratory of Colloid, Interface and Chemical Thermodynamics, Institute of Chemistry, Chinese Academy of Science, Beijing 100190, China
d.
University of Chinese Academy of Sciences, Beijing 100190, China

jiangj@nanoctr.cn

lts34@zzu.edu.cn

liumh@iccas.ac.cn

Received Date: 17 February 2023
Revised Date: 27 March 2023
Accepted Date: 29 March 2023
Available Online: 30 March 2023

Figures(5)

While enol-keto tautomerism has attracted great interest in Schiff bases and related compounds in solution and crystal states, the self-assembly of energy-unfavored keto form were scarcely investigated. Here, we report a keto-form directed self-assembly of a naphthalene-attached enantiomeric N-salicylideneanil analog L/DGG-Nap accompanied with a significantly amplified circularly polarized luminescence (CPL). It was found that LGG-Nap exists as a mixture of enol and keto form in monomer at a diluted toluene solution. The increment of the concentrations leads to the formation of predominated keto form, which subsequently triggers the self-assembly. Cryo-transmission electron microscopy (Cryo-TEM) revealed that a hierarchical assembly process happened upon increasing the concentration of LGG-Nap in toluene. Individual nanofibers formed at 1 × 10⁻⁴ mol/L and transferred into helical nanofiber bundles in 5 × 10⁻³ mol/L. Interestingly, while these is nearly no circular dichroism (CD) or CPL in the monomeric solution, the assembly showed strong CD and CPL. Remarkably, the dissymmetry factor (g_lum) was significantly amplified from zero in solution through the 0.005 in individual nanofiber to 0.1 in nanofiber bundles. This work demonstrates that the enol-keto tautomerism can be broken and trigger the self-assembly upon increasing the concentration, which can subsequently direct the chiral self-assembly and significantly amplify the dissymmetry factor of assembled CPL materials.
- Enol-keto tautomerism,
- Chiral self-assembly,
- Schiff base,
- Circularly polarized luminescence,
- Nanofiber bundle
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