Synthesis and characterization of optically active helical polymers based on 2,5-di(4′-formylphenyl)styrene

Zhiguo Zhu*, Junge Zhi, Anhua Liu, Jiaxi Cui, Xinhua Wan, Xiaofang Chen, Qifeng Zhou

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

Abstract

2, 5-Di (4′-formylphenyl) styrene was synthesized via Suzuki cross-coupling reaction of 2, 5-dibromostyrene and p-formylphenylboronic acid. In the presence of catalytic amount of glacial acetic acid, a pair of chiral nonracemic vinyl monomers, (+)-2,5-di {4′-[(N-(S)-α- methylbenzylimine)methylene]phenyl} styrene (M 1)and(-)-2,5-di {4′-[(N-(R)-α-methylbenzylimine) methylene] phenyl} styrene (M 2),was synthesized through the condensation reaction between 2, 5-di (4′-formylphenyl) styrene and optically pure α-methylbenzylamine. Optically active polymers were prepared via free radical polymerization of M 1 and M 2 initiated by AIBN or BPO depending on polymerization temperature. The results from specific optical rotation, UV-Vis absorption spectra and circular dichroism spectra indicated that the polymer obtained might adopt a helical conformation with a predominance of one helical screw sense. The polymerization condition had pronounced effects on the chiroptical properties of the polymers. Polymer with larger helical chirality was obtained when the polymerization was carried out in more polar aromatic media at higher temperature. Due to the steric hindrance of the bulky p-terphenyl groups, the main chain helical chirality formed during polymerization was thermally stable and displayed memory effect.

Original languageEnglish
Pages (from-to)875-883
Number of pages9
JournalActa Polymerica Sinica
Issue number9
Publication statusPublished - Sept 2007
Externally publishedYes

Keywords

  • Chiral vinyl monomer
  • Free radical polymerization
  • Helical conformation
  • Optically active polymer
  • Schiff base
  • p-terphenyl group

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