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Keywords:

  • Chirality;
  • Helical structures;
  • Self-assembly;
  • Nanostructures;
  • Phthalocyanines

Abstract

Three phthalocyanine derivatives with four peripheral chiral (S)-2-methylbutoxy moieties at the α or β positions of the phthalocyanine ring have been synthesized. The CD spectra of compounds 1 and 2, each containing four peripheral chiral (S)-2-methylbutoxy moieties at the α positions of the phthalocyanine ring, show CD signals in the Q-absorption region of the phthalocyanine chromophores. However, no CD signal was observed in the whole absorption region for compound 3, which contains four peripheral chiral (S)-2-methylbutoxy moieties at the β positions of the phthalocyanine ring. These results indicate the influence of the position of the chiral substituents on the chiral transfer and expression at a molecular level. Further investigation of the self-assembly behavior of compounds 1 and 2 revealed that the metal-free phthalocyanine 1 self-assembles into a nanocube whereas its zinc congener, [(S)-ZnPc(α-OC5H11)4] (2), self-assembles into helical nanobelts, which implies an effect of metal coordination on the morphology and handedness of the self-assembled nanostructures.