Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands

Blayne M. McKenzie, Adriane K. Miller, Rudy J. Wojtecki, J. Casey Johnson, Kelly A. Burke, Karis A. Tzeng, Patrick T. Mather, Stuart J. Rowan

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A versatile one-pot synthetic platform for the preparation of a range of functionalized 2,6-bisbenzimidazolylpyridine (Bip) derivatives is presented. This protocol significantly reduces the cost and time of previous synthetic routes, while facilitating scale up to multi-gram quantities in good yields (63-90%). The previous synthetic methodology was improved through judicious choice of the reducing agent and solvent in the reduction/ring-closing step. Via this platform, we also successfully accessed a mesogenic Bip ligand and herein report initial liquid crystalline properties of this derivative.

Original languageEnglish
Pages (from-to)8488-8495
Number of pages8
JournalTetrahedron
Volume64
Issue number36
DOIs
Publication statusPublished - 2008 Sep 1
Externally publishedYes

Keywords

  • Liquid crystal
  • Metal-ligand coordination
  • Supramolecular chemistry
  • Terdentate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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  • Cite this

    McKenzie, B. M., Miller, A. K., Wojtecki, R. J., Johnson, J. C., Burke, K. A., Tzeng, K. A., Mather, P. T., & Rowan, S. J. (2008). Improved synthesis of functionalized mesogenic 2,6-bisbenzimidazolylpyridine ligands. Tetrahedron, 64(36), 8488-8495. https://doi.org/10.1016/j.tet.2008.05.075