Synthesis and photoresponsive behavior of optically active methacrylic homopolymers containing side-chain spiropyran chromophores

Luigi Angiolini, Tiziana Benelli, Erika Bicciocchi, Loris Giorgini, Françisco M. Raymo

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Novel optically-active methacrylic homopolymers bearing in the side chain one or more chiral groups of one single configuration (based on the l-lactic acid residue) linked to the spiropyran chromophore, have been successfully synthesized and fully characterized. These intrinsically chiral polymers exhibit remarkable thermal stability, with glass transition temperatures in the range 100-130 °C and decomposition temperatures around 270°C. The chiroptical characterization indicates the occurrence of asymmetric induction on the electronic transitions of the side-chain chromophore related to the number of l-lactic acid residues interposed between the main chain and the spiropyran chromophore. In the presence of acid, these systems can be used to modulate the protonation of polymeric azopyridine moieties upon photoisomerization of the spiropyran group. In addition to UV-Vis spectroscopy, the proton transfer process occurring between the macromolecular components can be also followed by CD spectroscopy, the system thus behaving as a chiroptical switch.

Original languageEnglish (US)
Pages (from-to)469-477
Number of pages9
JournalReactive and Functional Polymers
Volume72
Issue number7
DOIs
StatePublished - Jul 1 2012

Keywords

  • Circular dichroism
  • Photochromic chiral polymers
  • Photochromism
  • Polymeric chiroptical switches
  • Spiropyrans

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics
  • Chemistry(all)
  • Chemical Engineering(all)
  • Environmental Chemistry
  • Biochemistry

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