Helical Self-Assembly of Optically Active Phthalocyanine Derivatives: Effect of Zn[BOND]O Coordination Bond on Morphology and Handedness of Nanostructures

Authors

  • Congcong Zhang,

    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    Search for more papers by this author
  • Lu Jing,

    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    Search for more papers by this author
  • Sha Lin,

    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    Search for more papers by this author
  • Zijuan Hao,

    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    Search for more papers by this author
  • Jing Tian,

    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    Search for more papers by this author
  • Prof. Xiaomei Zhang,

    Corresponding author
    1. Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211
    • Xiaomei Zhang, Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211

      Peihua Zhu, School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250100 (PR China)

    Search for more papers by this author
  • Prof. Peihua Zhu

    Corresponding author
    1. School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250100 (PR China)
    • Xiaomei Zhang, Key laboratory of Colloid and Interface Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shandong University, Jinan, 250100 (PR China), Fax: (+86) 531-8856-5211

      Peihua Zhu, School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250100 (PR China)

    Search for more papers by this author

Abstract

Two optically active phthalocyanine derivatives with eight peripheral chiral (S)-4′-(2-methylbutoxy)biphenyl moieties on the β-position of the phthalocyanine ring are synthesized. The circular dichroism (CD) spectra show signals in the Q absorption region for both compounds 1 and 2 in chloroform solution, indicating the effective chiral-information transfer from the peripheral chiral (S)-4′-(2-methylbutoxy)biphenyl side chains to the phthalocyanine chromophore at the molecular level. Their self-assembling properties are further investigated by using electronic absorption and Fourier transform infrared spectroscopy, transmission electronic microscopy, scanning electronic microscopy, X-ray diffraction, and X-ray photoelectron spectroscopy. Experimental results reveal the effect of the metal-coordination bond on molecular packing models in these nanostructures, which in turn results in the self-assembled nanostructures with different morphologies, from nanosheets for 1 to helical nanofibers for 2. In addition, good semiconducting properties of the nanostructures fabricated from phthalocyanine derivatives 1 and 2 are revealed by current–voltage measurements.

Ancillary