Worcester Polytechnic Institute Electronic Theses and Dissertations Collection

Title page for ETD etd-082405-155024

Document Typethesis
Author NameGokcen, Taner
TitleMolecular Engineering of Trigonal Octupolar Materials Based on 2,4,6-Diarylamino-1,3,5-Triazines
DepartmentChemistry & Biochemistry
  • Venkat R. Thalladi, Advisor
  • Keywords
  • hydrogen bonding
  • octupolar
  • nonlinear optics
  • crystal engineering
  • Date of Presentation/Defense2005-08-24
    Availability unrestricted


    Molecular engineering of some 2,4,6-(substituted biarylamino)-1,3,5-triazines and crystal data belonging to the products 2,4,6-(m,m’-ditolylamino)-1,3,5-triazine, 2,4,6-(p,p’-ditolylamino)-1,3,5-triazine and 2,4,6-(phenyl-p-tolylamino)-1,3,5-triazine were reported. Retrosynthetic analysis of trigonal octupolar networks led to the identification of tris-substituted diarylamino-triazines as molecular analogs of Piedfort units formed by cofacial dimers of 2,4,6-triaryloxy-1,3,5-triazine molecules. Synthesis of mono and diarylamiono triazines is achieved by coupling of the corresponding anilines with cyanuric chloride. Synthesis of diarylamines exhibiting different functional groups on two phenyl rings is attempted; the successful attempt in the case of phenyl-p-tolylamine is described. All the crystals obtained so far belong to centrosymmetric space group P21/c. Though none of the molecules retain trigonal symmetry in the crystal structures, pseudo-trigonal assembly of molecules is identified in some cases. The assembly of molecules within the crystals results in columnar structures formed by C-H..N and C-H..pi interactions.

  • Gokcen.pdf

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