• Fulltext

       

        Click here to view fulltext PDF


      Permanent link:
      https://www.ias.ac.in/article/fulltext/jcsc/129/02/0149-0156

    • Keywords

       

      Perylene bisimides; x-ray diffraction; axial chirality; density functional theory.

    • Abstract

       

      1,6-Diaminoperylene bisimide (1) was synthesized and characterized by single-crystal X-raydiffraction. To the best of our knowledge, this is the first time that the structure of 1,6-disubstituted perylene bisimide has been reported. The crystal belongs to triclinic, space group P-1, with a = 10.3966(10), b = 15.3398(16), c = 16.8495(17) Å, α = 79.490(4)◦, β = 87.055(3)◦, γ = 79.423(3)◦, and Z = 2. Compound1 possesses two intramolecular C–H· · ·N hydrogen bonds, which generate two S(6) ring motifs. The central perylene core of 1 is twisted with dihedral angles of 19.48(2)◦ and 19.50(2)◦; this twist configuration induces the axial chirality in this family of perylene bisimide chromophores. Density functional theory (DFT) calculations also show that the core twist angles of 1,6-diaminoperylene bisimide are larger than those of 1,7-diaminoperylene bisimide, which may account for the fact that the 1,7-regioisomer has a more extended effective conjugation length than the 1,6-regioisomer.

    • Author Affiliations

       
    • Dates

       
    • Supplementary Material

       
  • Journal of Chemical Sciences | News

    • Editorial Note on Continuous Article Publication

      Posted on July 25, 2019

      Click here for Editorial Note on CAP Mode

© 2017-2019 Indian Academy of Sciences, Bengaluru.