Preparation of optical active polydiacetylene through gelating and the control of supramolecular chirality

Abstract

Achiral diacetylene 10,12-pentacosadinoic acid (PCDA) and a chiral low-molecular-weight organogelator could form co-gel in organic solvent and it could be polymerized in the presence of Zn(II) ion or in the corresponding xerogel under UV-irradiation. Optically active polydiacetylene (PDA) were subsequently obtained. Supramolecular chirality of PDA could be controlled by the chirality of gelators. Left-handed and right-handed helical fibers were obtained by using L- and D-gelators in xerogels respectively, and CD spectra exhibited mirror-image circular dichroism. The PDA in xerogel exhibited typical blue-to-red transition responsive to the temperature and pH, while the supramolecular chirality of PDA showed a corresponding change.

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Correspondence to MingHua Liu.

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Duan, P., Li, Y. & Liu, M. Preparation of optical active polydiacetylene through gelating and the control of supramolecular chirality. Sci. China Chem. 53, 432–437 (2010). https://doi.org/10.1007/s11426-010-0067-2

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Keywords

  • diacetylene
  • low-molecular-weight organogel
  • induced chirality
  • supramolecular chirality