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Optical Activity of Homochiral Polyamides in Solution and Solid State: Structural Function for Chiral Induction.

Lingli Zhang1, Chenxi Zhang1, Wenjie Zhang1

  • 1School of Materials Science and Engineering, Zhengzhou University, Zhengzhou 450001, China.

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|August 29, 2019
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Researchers developed optically active helical polyamides using acetylated tartaric acid enantiomers and undecanediamine. These chiral polyamides exhibit distinct circular dichroism (CD) signals and helical structures in solid states, demonstrating temperature-dependent optical properties.

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Area of Science:

  • Polymer Chemistry
  • Chiral Materials Science
  • Spectroscopy

Background:

  • Optically active polymers are crucial for advanced applications.
  • Developing facile synthesis methods for helical polyamides remains a challenge.
  • Tartaric acid derivatives offer a promising chiral source for polymer synthesis.

Purpose of the Study:

  • To develop a simple and facile method for preparing optically active helical polyamides.
  • To investigate the chiroptical properties and helical conformations of synthesized polyamides.
  • To explore the influence of temperature on the circular dichroism (CD) signals.

Main Methods:

  • Protection of l- and d-tartaric acid hydroxyl groups to form l- and d-2,3-di-O-acetyl-tartaric acid (l-ATA, d-ATA).
  • Interfacial polycondensation of l-ATA, d-ATA, and achiral 1,11-undecanediamine to synthesize polyamides PA-l and PA-d.
  • Circular dichroism (CD) spectroscopy to analyze optical activity in solution and solid states.
  • Scanning electron microscopy (SEM) to visualize helical aggregation in solid states.

Main Results:

  • Successfully synthesized enantiomeric helical polyamides (PA-l and PA-d).
  • Observed distinct negative and positive mirror CD spectra for PA-l and PA-d, respectively.
  • Demonstrated stronger optical activity and unique CD signals in the solid state due to helical conformation.
  • SEM confirmed left-handed helical aggregation for PA-l and right-handed for PA-d.
  • CD signals showed temperature dependence in dilute solution but were stable in the solid state.

Conclusions:

  • The study presents an effective approach for synthesizing optically active helical polyamides.
  • The synthesized polyamides exhibit significant chiroptical properties arising from their helical backbone conformation.
  • The findings highlight the potential of these helical polyamides in applications requiring specific optical activity and chiral recognition.